After I wrote all this mess, I decided to break it out from the regular day-to-day stuff that makes up the bulk of sounds familiar, just to spare the typical audience from something they likely wouldn't be interested in.  But for those who may get down with the music/audio/technical junk, here's some.

Well folks, I thought I had it all.  A while back when I got the new 2009 Beatles remastered catalog in lossless FLAC format I figured I had the best sounding version of the stuff to be had by humans. I was even super happy that I was able to losslessly transcode the FLAC files into Apple's own lossless audio format for pristine playback on the iPod (I know, no comments about my 6G iPod Classic's crappy DAC or sound quality in general here, please).  Anyway, put short - I was pleased that, on my portable device, I had the best-sounding versions of the Beatles' records you could get.

Then EMI (not Apple, and the subtle distinction is important here for Beatlemaniacs) goes ahead and releases the entire catalog again in digital format, via a special USB key, and this time they offer a "24 bit"  lossless FLAC option.  What does this mean?  I dunno... not a lot unless you want me to get way technical... oh wait, you do?  If you wanna skip the techy stuff, move forward to the very last paragraph here ("Goodnight") and just know that the 24 bit version is, for some scientific reason, better than what I had previously.  For the smarty-pantses out there...

Regular readers tuned-out?  Gone?  Good.

See, normal, CD-quality tunes have a bit-depth of 16 bits per sample (a sample being sized as 1/44,100th of second).  Higher-definition audio, such as DVD-quality audio, often comes at at an increased bit-depth of 24 bits per sample, and a smaller sample size (sometimes 48 kHz, sometimes 96 kHz, sometimes as much 192 kHz).  If you're nerdy, you can think of it as an analog-to-digital thing, trying to take enough discrete points of digital data to accurately represent a continual analog sound.  The more often you "record" the analog sound, and the higher "resolution" in which you make the recording can be thought of, respectively, as sample-rate and bit-depth.  (And for the real nerds those last two links are to a couple far-better explained Wikipedia articles on the subject.)

Anyway, EMI's straight-to-digital release upped the Beatles catalog ante by offering the lossless files in 24 bit format (albeit still sampled at 44.1 kHz, which some maintain is akin to a cliffhanger ending in a summer blockbuster... leaving open the door for yet another "upgrade" to a higher quality version of the set at a later date).  Oh great; this now means that my heretofore "best quality" 16 bit files on the iPod are, in fact, now trumped.  And while folks will argue with me about an iPod's ability to, with any noticeable difference in sound quality, reproduce 24 bit audio... I of course want to get these new recordings on my trusty portable device.

Problem is getting 24-bit FLAC files converted over to 24-bit ALAC (m4a) files - using Windows - hasn't historically been the easiest thing in the world. At this point in time, it's rather trivial if you're in the MacOS environment, but quite a bit more tricky in a Windows environment (especially if you prefer open-source stuff or you're not overly-anxious to spend money on a pay-for piece of software to do the task).  If you're a Mac person, you've got XLD or Max at your side and'll have hardly any issues getting high-def stuff onto your iPods (provided you're stubborn like me and want to do it regardless of whether or not the playback quality warrants it).  If you're a Windows user, you're options are significantly more narrow.

However, I'm here to report my personal success in the hopes that others out there may share in it.  See, just last week the venerable application dBpoweramp released a version of their great conversion software that supports encoding of 24 bit Apple lossless files.  What's more, the software does the conversion in a batch format, from the original directories, in mere seconds, and it's completely free for a 28 day trial period - no strings attached.  Wonderful.  And, as a check, the final files imported into iTunes show 24 bit / 44,100 Hz as expected (and I'm sure would match the sampling rate on a 96 kHz file as well).  Losslessly perfect!

For what it's worth, as long as you can get files encoded into an Apple container, an iPod classic will indeed support 24 bit playback (I have the 6th generation 160GB, your mileage may vary).  And, even with the internet, it's pretty hard to nail down the sampling-rate limitations... but from experience I can tell you my 6G classic has no issues at all with the 24 bit / 44.1 kHz Beatles ALACs.  Apparently, however, the iPod does have a sampling-rate ceiling of 48 kHz, and reportedly trying to load anything sampled at a higher rate than this onto your iPod will cause iTunes to spit it right back (yet my Apple TV is able to play 24 bit / 96 kHz files via the optical output, which is fantastic).

So for me, I'll ignore the audiophile mantra of "you'll never be able to tell on the iPod anyway," delete my old 16 bit ALAC files from the iPod, and go with my newly-FLAC-transcoded 24 bit / 44.1 kHz ALAC versions of the Beatles' catalog for portability.  I mean, even amongst all the stuff I read online about the quality of the iPod's DAC, there's reason to believe you might be able to tell a difference.  But at home, I'll try loading the ALACs onto the Apple TV and playing them back via optical to the surround system for the "best" listening... (since I don't want to have to buy one of those mega-expensive iPod DAC bypassing docks/transports anytime soon...).  Anyway, I've said it before: I'm no audiophile.  I obsess about it, but, when it comes down to it, I can't hear the difference.

Anyway, if you're a Windows user and dBpoweramp worked for you, you'll likely end up like me and buy it despite doing all you needed to do with it long before the free trial expires... I mean, it's worth it  - and down the road when more stuff comes in higher-definition format you're gonna want to be able to re-encode on the fly anyway.  Drop me a line if you had luck with it, or go buy it... whatever.

I got some Beatles to go listen to...

Goodnight.

If you're viewing the page via your iPhone or Android device today, you've likely noticed that I installed a much more mobile-friendly theme that takes over when the page is viewed in a mobile browser.  I like it a lot, and it's actually what inspired me to change up my current desktop theme (the main look and feel of sounds familiar).  I haven't done this in a long while... but my current theme was kind of clunky compared to some of the more modern themes.

My goal was to maintain as much of the look and feel of the site as possible while taking advantage of something less hacked-together (I still have to go through and reformat some of the more kludgy CSS remnants, but I'll get it all modernized soon enough).  I think it's mostly in-place now, the only drastic change being my decision to drop the years-old header logo... which meant ditching the Bible-times trumpet man image Ben stole for me off the internet way back in 2003.  Sayanora, trumpet man.

OK enough website junk.  Let's talk about something better.  Maybe something funny... Oh, I know!

Sunday evening this past week my daughter spent nearly five minutes explaining to me the wonder that was her Halloween-acquired Ring Pop.

See Dad, it's like ring but you can eat it like a lollipop.  It's candy.  You put it on your finger like a ring and it's pretty like jewelry but it's also candy like a lollipop.  See?  See it on my finger like a ring?  But watch, Dad!, look with your eyes!, see... I can... mmmpphh... see, I can lick it like a lollipop.  Isn't that neat, Dad?  Dad... did you see?  It's a Ring Pop.  It's called that because it's a ring and a lollipop.  Dad.  Dad?

About two explanatory sentences into her rant, I started laughing a little.  By the third or fourth recitation of her stark wonder, I had all but lost it and was cracking up.  Sharaun, sitting opposite me on the other couch, was also laughing.  By the end, I was playing with her (I think she figured it out).  "But wait," I'd stop her to interject, "Is that thing a ring, or a lollipop?"  Aaaand we'd start all over again.  Good stuff.

Changing subjects...

Recently, I've started using the track rating feature on the iPod.  I never really used the functionality before, for a couple main reasons: 1) I pretty much only put music I like on the iPod, so I would hope not to find anything less than "middlin'" were I to do a "rating audit" or somesuch and 2) I don't use iTunes to manage my music, so the track rating metadata would only live on my iPod and not be transferred permanently back into my collection.  If my iPod ever went south or I had to reload tracks off disk, I'd lose the ratings data anyway, so I've always considered it fleeting and useless.

Over time, my mind has changed somewhat on each point.  Yes, everything on my iPod is there because I at least "like" it.  But, as I've learned being a manager at the sawmill, even a group of top-performers has a bottom performer - regardless of whether or not that person is generically "good" or not.  Same with a huge batch of "good" tunes, I suppose.  Even if I like it all, there are some tracks that deserve a star or two more than others.  I figured that exploiting the natural strata of my tastes might actually make for some neat ratings-based "smart" playlists.

Furthermore, about a year ago I bought some software that promises it's able to make a complete, hardware/firmware agnostic, restoreable backup of my iPod.  The idea being that, as long as I keep up with the backups, were my iPod ever upgraded, lost, or ruined, I could restore it to its previous state - including track-by-track metadata.  Still, ratings wouldn't get sync'd back into my master collection on disk - but I gave up on this a long time ago after a couple failed migration attempts.  But, at least I could carry the ratings metadata through an iPod crash or upgrade... better than nothing.

Anyway... I'm trying it out.  Why not?

Goodnight.

Well, not on purpose...

See, Keaton was sitting in a chair with her back to the pool, eating an apple.  We were at a poolside birthday party and the swimming part had ended with the sun going down, so I was out of my trunks and back into my shorts and t-shirt.  And, properly dressed, I also had my iPhone and wallet in my pocket.  The scene was set.

Playfully, I approached Keaton under the guise of the Tickle Monster, arms outstretched and growling slightly, fingers clenching and flexing just looking for some good ribmeat for ticklin'.  I remember her smiling as I approached, shrinking back into the chair, and sticking her feet out to push me away.  Only, Newton's 3rd law says that, as much as little Keaton's feet pushed me away from her, my thighs pushed back on them in equal proportion.

Yup: Her chair leaned back and toppled.  And, in a flash, I could see the chair sinking into the shallow end of the pool, and remember vividly seeing Keaton's arms reaching wildly for the surface and her hair billowing in gravity-free plumes under the water.  Although it seemed like slow motion, my next awareness was being in the water.  As I grabbed her under the armpits and hoisted her above the surface, she had her mouth open and I could see bits of chewed apple inside.

She was crying, but not gulping or choking or gasping; I honestly don't think she had enough time to even try to take a breath before I got to her, and that she likely held her breath that long on instinct alone.  She clung to me and dripped.

Sharaun was standing next to me in the water, I actually think she beat me into the pool (also fully clothed) but couldn't get to Keaton for the chair.  Immediately after pulling her out of the water Sharaun wanted to take her from me and hold her.  Without thinking I passed her over, knowing already that she was fine (if a little shook up), and began climbing out of the pool.  Only then did I realize...

... the iPhone and wallet were still in my pockets.

I pulled out the phone and checked: dead.  In an attempt at playing humor for the watching folks, I chucked it into the grass in front of me - visually acknowledging its new uselessness.  In that moment, my thought was that my daughter was safe (if a bit wet) in the arms of my wife behind me - and a work-purchased iPhone was a small price to pay.  (Of course, in the next few days I'd try like crazy to resurrect the thing... fruitlessly, I might add.)

Monday I went down to the Apple store and got a new phone.  $199 later and I'm back up and running.

Worth every penny (not talking about the phone).

Happy Friday-minus-one my fellow internet lurkers.  I talk music and politics today, although I think I weave the taboo topics in smartly enough that you'll enjoy the narrative wrapped around them.  So, give it a try, wouldja?  Thanks.

I'm happy to share that I seem to be on the mend from my brief battle with a hit-and-run stomach sickness earlier this week.  And, even if it did force the cancellation of a long-planned trip to Oregon for some important (no, seriously, I missed something important) work-business and some even more-important family-business, I'm glad to share that I am once again comfortable enough to willfully pass gas without first heading to the bathroom.

Being at home today, and feeling much better than yesterday (and worlds better than Monday), I had some idle time on my hands.  I decided to try something I've been considering for a long time: Importing all my music into iTunes so that I can actually sync my Apple devices (iPod and iPhone) as they are designed.  So, I undertook that Herculean effort.  And, I'll stop talking about it here now because I've broken off the detailed tech-heavy explanation into it's very own blog entry you can read below (unless you're an uber-nerd though, I don't really recommend it).

Guys, guys, guys.  There are only a few unsolved musical mysteries left for me to ponder.  And, tonight, I totally solved one of the longest-running ones.  While I was sitting here typing, my iPod happened to shuffle up a live performance by Van Morrison (hey, it's a 1-in-42,000 shot, them's some odds!).  Now, this isn't just any live performance, this is an incredible, amazing, vibrantly "alive" live vetting of Van's "Summertime In England.  And, it's a recording that I've been obsessed with for years.  Let's tell the story, shall we?

Back in middle and high school, my best buddy Kyle was my musical sage, muse, encyclopedia, and conduit.  For a time, I got everything through Kyle, who himself got it all from his father by way of dubbed cassette tapes in the mail.  In a previous longwinded entry, I wrote about my "Kyle connection" thusly:

When I met Kyle after we moved to Florida, things exploded. With the influence his dad had on his extremely-mature-for-his-age and varied musical tastes, and the mainline connection to his dad’s collection in Texas (via dubbed cassettes again, but of course), my horde of lovingly hand-labeled 90min Maxells flourished.

Ahh... still as delicate a prose as the day I penned it, and just as accurate too.

Anyway, one of those recordings scored via a dubbed cassette from Kyle's dad was a live version of a Van Morrison song before then unknown to me.  All I knew was that when I put on that tape and listened to that eleven minute orgy of musical and lyrical genius, I was transported.  Smiles creased my face unbidden, and the tune seemed to mate perfectly with the Fall weather of the season in which I first heard it. I was smitten from the moment I heard it, not even knowing the name of the tune.

I can remember vividly driving to Sharaun's house early one Saturday morning in my little Red Nissan (perhaps it was still my parents' litte Red Nissan at the time, actually).  I had the windows down and the cool Florida air (a welcome rarity for the few months we get it) streamed in as I listened to the tape.  The saxophones swelled as I crossed US-1 towards the river.  I remember we were headed to a pancake breakfast at McDonalds, I think to raise money for her soccer, or volleyball, or maybe it was softball team (Sharaun is the jock in our family).

The point being, that song was indelibly inked into my mind in that moment.

Somewhere along the road, as things transitioned from tape to CD, I put that well-worn cassette away.  And, eventually, somewhere in my college-years moves from apartment to apartment, I lost it altogether.  I never forgot that song though...

Several years later, after marrying Sharaun and moving to California, I decided I wanted to hear that song again.  Over the years, I'd done a fair job collecting a bunch of bootlegs - and I'd always been keen to pick up a new illicit Van Morrison recording in hopes my fabled song would be included.  Although I never did find the song, I had long before been able to identify the name of the track as "Summertime in England."  Unfortunately, the song is a staple of many live Van performances - and trying to find a particular version based on vague memories of between-band banter just wasn't that easy.

Believe me, I tried.  I e-mailed die-heard Van collectors every detail of the show I could recall.  I mentioned that he thanked the members of the band by name, and that he did this echoed lyrical interplay with another vocalist during the performance, where one guy copied the other guy almost at the same instant he sung his line.  They did the same thing with the guitar, I noted.  Not a bad level of detail from a then musty memory, but I had zero luck in locating the actual performance I was after.  Don't get me wrong, I did manage to acquire ten or so other fantastic live versions of the song which kind collectors guessed might be the one I was after... but no paydirt despite my hunt.

Then, finally, out of frustration, I decided to cut to the chase.  Sometime in 2004 or so I decided to e-mail Kyle's dad directly and just ask him about the performance.  I wondered, in my e-mail, if he recalled where in the world he got the tape... or did he even know what performance I was referring to?  I figured going to the source was my best option.  Turns out Kyle's dad knew instantly exactly which song I was referring to (of course he would, he's the same as me in that way).  However, he said he "thought" he recalled dubbing his cassette off an old VHS he'd recorded from a television broadcast, but could remember nothing more than that.

He did, however, still have that dub and promptly offered to send me a CD-R copy.  I supplied my address, the CD came, I thanked him profusely and dutifully ripped the now legendary-to-me performance onto my iPod... which brings us back full-circle to it being shuffled up tonight.

As my face beamed listening to the song again, I began wondering about typing some exact phrases from the band banter into Google... just fishing.  Turns out I got a single hit on the phrase "Mr. Morrison" "Mr. Hospitality."  It led me to a message board where it mentioned a "Beacon '89" show.  A few Google searches later and I'd landed on a YouTube clip of Van Morrison and his band playing "Summertime In England" live at the Beacon Thearer in New York City in November 1989 (too bad it's clipped at the beginning).  And, wouldn't you know it... it was the song.  That's right, the version I'd been looking for forever (and, I suppose, had actually "found" a few years back - although still not fully knowing all the background).

And, with a little more digging I'd turned up the fact that a two-disc soundboard quality bootleg of the show exists under the title Inspired Evenings.  Minutes after that, that very bootleg was streaming it's way, via a series of bits and bytes, onto my hard drive - from the very nether regions of the internet.  And now it's done, one great mystery solved.  Next - the unidentifiable mixtape of 1992... I swear I'm gonna crack that case one day... I just know it.

OK, end music stuff.

Before I go, I wanted to remind everyone (even if you voted in a recent primary) to go ahead and double-check your registered voter status.  With deadlines looming in nearly every state, it's in your best interest to confirm your registered status so you have no surprises at your polling place come November.  And yes, I mean this regardless of whom you intend to vote for

To check your status in your state, use the this handy website (quite a few states have quick and painless online status checking).  Happy democracying!

G'nite.

Are you like me in that you see some advantages to using iTunes for managing your music collection and synchronizing it with your various Apple devices, but are completely underwhelmed by its basic functionality?  If so, this entry may be able to help you.  If not, then... well... not.

I have a huge collection of music on disk (~300GB) that I maintain manually and am very anal about.  I like the way my files are organized, I like being able to reorganize and re-tag them whenever I want with my choice of 3rd party tools (Tag&Rename, The Godfather, Windows), and I have an extremely anal methodology for pre-processing and merging newly acquired files (files not acquired via iTunes)  to the "master" location.

However, despite my hands-on tendencies when it comes to controlling my digital music collection, there have been several times in the past when I've wished I had my entire library present in iTunes (all explain why a little better below).

For a while now I've wondered if there's an "easy" way to have the best of both worlds.  To have my music "in" iTunes while not giving up my low-level control of the actual files.  To be able to work with my media through whatever means I desire and not have these things interfere with each other.

Turns out there was a solution, at least for me, although the "easy" part might be subjective (I'm willing to go to great lengths to manage my music the way I want to, you may be less so after reading this diatribe).  Through the following I'll document my journey to playing nice with iTunes, and hopefully this might help some other anal music collector looking to do something similar.

Let's start off by documenting my situation:

My intended goal:

Start using iTunes as the default "library manager" for all my music.

Why do I want to do this?:

There are several advantages, as I see it, to having iTunes manage my music.  All of these are based on the fact that I'm using Apple devices (iPod Classic & iPhone 3G) to actually listen to my music (the benefits of iTunes as a library manager kinda drop off if that's not the case).  Some of the advantages:

• When you manually manage music on your iPod sans iTunes, any metadata generated on the iPod is not tracked back into your master on-disk library.  If I have my library in iTunes, however,  using the "sync" option means metadata generated from listening habits on the device is now "backed up" into my iTunes library file and I won't lose it should I upgrade to a new device (more on that below).
• I also like that by taking advantage of the "sync" feature, I can "backup" things like smart playlists, which I currently have only on my iPod (since they make no sense in an iTunes that has no library, as mine now stands).
• Again, using the sync feature means that any metadata changes I make to my files on disk are automatically carried over to the files on my iPod.  When you manually manage adding music to your iPod/iPhone, you lose this "connection" to your master on-disk library.
• If I buy a new iPod, I can simply plug it in and re-synchronize my entire library with a click (including that oh-so-important-to-me track-level metadata I mentioned above).  When you're manually managing music on the device, this is not an option.  So, if your iPod dies or gets lost, you have to rebuild the collection on it by dragging and dropping everything back.  Painful.  This is probably the single most important thing to me, as I've gone through it before.

Success criteria:

1. I don't want the physical structure of my files on disk to be modified in any way.  I don't want anything renamed, reorganized, re-anything.  I want my file structure on disk to remain completely unchanged through this big iTunes import.
2. I want to retain "manual" control of my files on disk.  This means having  the ability to rename, reorganize, re-tag, move, delete, etc. these files using applications/methods other than iTunes.  I want to be able to do this without messing up my iTunes library (creating "orphan" entries, out-of-sync pointers, etc.).
3. In addition to the manual control I'd like to maintain in #2 above, I'd also like to be able to use iTunes to manage files if and when I feel like it.
4. If, per #2 above, I've manually deleted, moved, or changes files using a 3rd party application or Windows (in other words, not using iTunes) I need iTunes to be "smart" enough to sync up with what's now on-disk.  In other words, I want my iTunes library to always mirror my manually-controlled library on-disk.
5. Since I don't get my music from the iTunes store, I also need iTunes to be "smart" about watching my master folder on disk for newly-added files.  When it finds something new, I expect it to be added to the library.   Again, in other words, I want my iTunes library to always mirror my manually-controlled library on-disk.

I know, it may seem picky.  But that's what I want.

Resolution:

So, was I able to meet all these criteria above and successfully "merge" my music-management process with an iTunes-managed library?  I sure was.  For those interested, I'll walk through the criteria and let you know how I achieved each one to my own satisfaction:

1. iTunes actually plays pretty nicely here, allowing you to uncheck the "Keep iTunes music folder organized" and "Copy files to iTunes music folder when adding to library" options under Preferences|Advanced (see image below).
   For me, I needed to uncheck both of these (the former to satisfy my criteria #1, the latter to satisfy my criteria #2).  Criteria met.
2. Unfortunately, when you use iTunes to manage your music - iTunes assumes it's the lone player in this game.  You can go modify files on-disk to your heart's content, but none of these changes will be reflected in iTunes unless you re-add the modified files to your library.  This is the main problem I have with iTunes, it refuses to acknowledge you might do things to your music outside of iTunes... I did, however, manage to meet this criteria, for the how - see "the panacea" statement below.
3. This one is easy if I can meet 2, 4, and 5.  All I need is for iTunes and my manual processes not to step on each other.  This is more a requirement of my manual process than of iTunes.
4. Again unfortunately, Apple expects that if you're adding or deleting music, you're doing it via iTunes.  It makes no accommodations for music file management via other means.  For how I solved this, see "the panacea" below.
5. Again again unfortunately, Apple refuses to accept the fact that people might get their music from anywhere other than the iTunes store, and iTunes is incapable of monitoring folders in this way.  Fortunately, there are some 3rd party applications that can do this for you -  See "the panacea" below.

The panacea: How I met criteria 2-5:

So, how'd I do it?  Believe it or not, there are a couple free pieces of software out there on the great wide internet that can accomplish these things for you (and me).  iTunes Library Updater and iTunes Folder Watch.  Both of them do essentially the same thing, but I'll tell you below why I chose the former of the two  as my solution.

First up, what do these applications do?  Simply, they allow me to force iTunes to monitor a folder or multiple folders on disk for changes, and synchronize my iTunes library to the folder(s) (without modifying the files themselves on disk).  While this is exactly what I want, there is one major difference between the way each operates.

While both applications keep track of newly added or removed files in your watched folder(s), only iTunes Library Updater includes the ability to monitor track-level metadata (ID3 tag) changes as a synchronization criteria.  For instance, if you've used a 3rd-party application (Tag&Rename, etc.) to change some tag data or add album artwork to your MP3s on disk, iTLU will notice this, and update the files for you in iTunes.  iTunes Folder Watch does not include this level of functionality.  So, if you change ID3 information outside of iTunes, you have to acutally play or "get info" on the updated files in your iTunes library to get a refreshed version of the tag information.

For this reason, I consider iTunes Library Updater the better solution, and will continue explaining my "panacea" in the context of using it rather than iTunes Folder Watch.

To make this whole thing work, you simply configure iTLU with the folders you want to be automatically monitored and mirrored into your iTunes library (along with several handy advanced criteria regarding the actual sync process) and hit "go."  And, since iTLU comes with a command-line interface, the whole process can be scripted into a batch file that you can add to your Windows Scheduled Tasks (I won't write detailed instructions for this, as someone's already done a great job over here).  It's in this way that I have my iTunes library automatically synchronized to my master on-disk library every night while I sleep.

Before you move along here, I would be remiss if I didn't note the fact that the iTunes Library Updater application is no longer being actively developed.  In fact, it hasn't been updated since something like iTunes version 6.  So, the fact that it continues to work with the current version of iTunes (versions 8.x as of writing) is pretty much gravy.  Bottom line, future changes to iTunes could completely break iTunes Library Updater at any time. This is a risk I am taking.

My thoughts are that if and when this day comes, I will simply have to switch to iTunes Folder Watch, wait for Apple to implement in iTunes, break down and code something myself, or give up on iTunes for good.

OK, but what's the process?:

Wow, you actually read this far?  I'm shocked you're still with me.  If you're way down here, you probably have a good idea how I did my whole migration, but just to make it simple I'll sum it up in some easy-to-follow steps for you:

1. Download and install iTunes Library Updater.
2. Configure iTLU to point to the music folders you desire it to mirror into your iTunes library, and check whichever options you want.
3. Save your configuration as an iTLU "profile" to ease repeated future use.
4. Hit "Start" in iTLU and crack a beer as the application imports everything into your iTunes library.
5. Make a batch file that invokes iTLU using the profile you saved in step 3 above (using the console version's /p switch), and add this batch file to your Windows Scheduled Tasks as often as you'd like (I do it every single night).
6. Continue enjoying your Godlike control over your digital music files while simultaneously taking advantage of the benefits that having your collection in an iTunes library brings.

Conclusion:

And, as for getting your music into iTunes, that's it.  If you're satisfied then I think you can stop reading now.  But, because I tend to write a lot... I actually have a few more points to make that, if you've come this far, you may be interested in reading.

If you're done with me here, I appreciate you hanging in there.  If you've got comments or suggestions (particularly if you've got some super-simple "better way" than what I've outlined here), please don't hesitate to drop a comment below and let me know.  Hope it helped, take care.

Some further notes (for the really anal):

First, a big postscript to all you other "manually manage" people out there.  I know you, you're just like me.  As you read this, there are exactly zero files in your iTunes library.  You drag-and-drop everything you need right onto your iPod and only use iTunes as the facilitator for that.  But, if you're an advanced listener like me, you might also have some on-iPod smart playlists defined that do super-fancy stuff with the tunes you've manually added to your beloved device.   And, one disadvantage of the "convert to iTunes" method I've outlined above is that you won't be able to import any metadata that's been generated on your device (through your regular listening) into your new iTunes-based library.

You may be thinking it would be nice to "retrieve" this data before bringing your on-disk collection into iTunes, so that you can continue to build data around your listening habits and drive your smart playlists.  And, you're right, it totally would be nice to do this.  I, however, made a big concession on this point when doing my huge "gonna start using iTunes" decision.

See, I too, have always said that if I were to make the conversion to managing my entire library via iTunes I'd like to be able to preserve all the metadata I've accumulated listening to my manually-added tunes on the iPod (meaning I'd like to be able to keep things like "play count," "skip count," "last played," etc.).   And, you actually can do this.  Yes - you totally can.  See, you can use a piece of software called CopyTrans to first grab all the music off your iPod and into iTunes.  As it does this, it will copy over your precious metadata too (it works, I tried it).

The only issue with this is the extra overhead it adds to the above process...  See if you're a "manual manager" like me, once you've extracted the files (and their associated metadata) off your iPod and into iTunes (which also means they physically went somewhere on disk), you're going to have duplicate copies of those files in your master collection.  And, since the metadata you want does not "live" inside the MP3 tag data itself, but rather in the iTunes library XML file - you'll now need to somehow get rid of those metatdata-less dupes in your mater collection (in favor of the metadata-associated versions now living on-disk from the CopyTrans import).

Your head hurt yet?

To try and simplify the explanation, you now want to keep the iPod-extracted files and remove the duplicate files from your master collection.  This is a pain, especially if you have a 160GB iPod Classic like me.  Oh, it's doable... it really is, and you could keep and carry-over all your on-iPod generated metadata... but it's just too much work.  So, in my case, I just decided that my big conversion to iTunes would be accompanied by a loss of all my on-iPod metadata.  That simple.  Kinda crappy, but better, in my opinion, than the time-consuming multi-step alternative outlined above.

All part of the paradigm shift, I figure.

Second, I can't help but assume that, if you're reading this article and your digital music collection means this much to you that you may also be facing another problem I've worked through.  Specifically, now that you've got your entire collection into iTunes, how the heck do you manage what actually goes on your iPod and what doesn't?  It's the classic "my iPod is too small for my music" problem.  I'll try and address that in a future entry, because it's just too long to work through were it tacked on here.

That's it!  Thanks for reading, take care!

If you've read some of my banal iPod-related ramblings here before, you'll know that I'm a big fan of using iTunes/iPod Smart Playlists to configure interesting musical selections. One of my favorite Smart Playlists I have on the 'Pod is the "Unheard" list. A simple playlist that grabs all items where the "playcount" equals zero, and theoretically eases the task of making sure I've heard all those gems lurking in the back corners of my disk. The only problem with the playlist, and, in fact, with any shuffle-based playlist, is that it gets skewed heavy towards artists that are better represented on the iPod. Now look, I don't need a lesson in statistics here, OK? I realize that, if out of 500 tracks on my iPod, 250 are the Grateful Dead, I'm going to see the Dead pop up pretty often in a true shuffle (as would be the case with my randomly-picked "unheard" list).

Problem is, I actually want to have every single Dead Dick's Picks album on my iPod, just on the off chance that I can impress some Deadhead by saying "You bet I do" when they ask, passing the bong, "Hey man, do you have that '75 Berkely gig, you know, the one where Donna Jean couldn't hit the high notes in 'Rain and Snow?'" And, I want each of the twenty-nine takes it took The Beatles to get "Hold Me Tight" right, not to mention all fifteen live versions of "Over the Hills and Far Away" Zeppelin performed on their '73 US tour. I really do want to have all that on my iPod, all the time. I don't want, however, the thousands and thousands of songs that pepper my iPod as a result of that fanaticism to "overpower" all the other stuff when shuffling. Here's where you say, "Too bad Dave, you can't have it both ways."

Oh but I can! Here's how I managed to limit the number of tracks per artist in a shuffled playlist.

First, make a smart playlist of all your music minus the overpopulated artists. I did this based on the catch-all criteria of track-time being greater than zero, and then filtered out the Grateful Dead, Beatles, and Led Zeppelin (my three most heavily populated artists). You could just as easily do it basing it off the iPod's default "Music" playlist (which contains your entire library). However you do it, what you should end up with is a playlist containing your entire collection minus your most heavily represented artists.

Next, make a separate playlist for each of your overpopulated artists, limiting the number of songs to a reasonable number (I chose one hundred) chosen at random. Do this by using the "artist is" criteria along with the "limit to" filter. In my case, this means I have three playlists: Beatles, Zeppelin, and the Dead, each limited to one-hundred songs chosen at random from the thousands available for each artist.

Finally, create a new playlist that pulls music from the playlists you just made in the previous steps (you can use "in playlist" as a criteria for a playlist). You'll need to make sure that you set the match criteria to "any" instead of "all" on that last one, or you'll get a playlist with zero items. This newest playlist is essentially your entire collection, including your overpopulated artists, but limiting them to one-hundred (or a number of your choosing) tracks each. And, from now forward, instead of basing all your shuffle-themed playlists around the iPod's default "Music" playlist, you can base them off of your new limited-representation list. Voila!

Postscript: If you do create sub-lists such as my one-hundred item random ones described above, you may notice that, over time, these playlists are not magically “refreshed” with new random tunes via iTunes. Despite the more-than-somewhat misleading name, “live updating” does not mean the playlist will choose a new batch of random songs, it means only that, when you add more songs to the iPod/iTunes that fit the smart playlist criteria, they’ll be accounted for and captured. If you’re looking to get some form of “auto refreshing” for your random tune selection (as I was, makes things more interesting), you’ll need to add some further elimination criteria to the playlist. I chose to add a criteria that “last played” is “not within the last” one week. This way, once a song is filtered into the playlist and you’ve heard it recently, it’s eliminated from the playlist and replaced with another (per the “limit to XX tracks” tickbox). Anyway, hope that helps.

You can likely think of all sorts of other limited-shuffle tricks you can do with playlist-combining, which makes using Smart Playlists a fun way to experience your music in different ways. Too bad Apple hasn't added a way to "hide" certain Smart Playlists from showing on the iPod. It would be neat to be able to mask out the ones that are only "supporting" lists as building blocks to a final one (like the hundred-track ones required as interim input to create the final list above). Maybe with a new firmware, eh?

See ya!

Know how I know I’m old? Check this out.

The other day, on the way to work in the morning, I stopped off at Chevron station nearby my house to gas up. I tend to stop at this particular Chevron often, as it’s close to the house and lies on my home-to-work route. While standing outside in the grey morning cold pumping petrol into the Ford, I noticed a station worker scurrying around the pump area in a hunter-orange vest with reflective green accents thrown on over his sweatshirt. He was busy picking up trash, emptying bins, and just doing a general “checkup” of the pump station area. I took notice, in part, because I realized that it wasn’t the first time I’d seen an attendant doing such a thing at that station. In fact, as I began to think on it a little more, and take a closer look around the station grounds, I began to notice that this particular Chevron station was actually quite nice: the pumps are never broken, it’s always clean and functional, the ads and posters and flats pitching carwashes and Techron and Chevron credit cards are new, clean, and relevant, etc. I started thinking about how, as gas stations go, this one was actually pretty nice.

Now, this is the part where I realize I’m old.

When I got to work around 8am, my pleasant Chevron experience was still fresh in my brain. Without really thinking, I found myself directing Firefox to the Chevron page, and looking up the e-mail address for customer feedback. And, again, before I could really stop myself, I had written a three-sentence piece of unsolicited, positive, encouraging, feedback to Chevron. Apparently, as old-age silently took over my brain and directed me in these abhorrent actions, I had also taken the time to look up the four-digit “store number” of the location I’d earlier fueled at, and called it out by name in my missive. After I “woke up” from my geriatric haze, I'd realized what I'd done and immediately logged onto MySpace, sent some text messages, and played "the choking game." It was close, but I was just able to reclaim the coolness of my youth.

What the heck is happening to me? Writing letters to companies? That's something my dad would do. Next I'll be calling senators and decrying the rampant depravity of today's youth. I am so old.

Oh, and before I go, I'd like to clear out another half-written blog by sloppily pasting in this e-mail exchange I had the other day with Ben. I thought it was funny, maybe you will too.

_____________________________________________
From: Dave
Sent: Wednesday, November 28, 2007 8:29 AM
To: Ben
Subject: I can't believe it

So, yesterday I re-copied all the tracks off my old iPod onto my PC (mostly, to have a permanent backup). Then, I restored my new Classic to factory state, and dragged all the backed-up music onto it via iTunes. Four hours later, all the music was on my iPod. Happy, I unplugged the iPod and went to browse through Coverflow, only to be greeted with the “Choose Language” menu. OK, English.

What?! No music?!

Sure enough. There was nothing on the dang thing. I had to restore it again and re-re-copy it all over. Why do I love this flaky POS? Just because it looks sexy? Am I hypnotized into brand loyalty by those shadowy commercials?

_____________________________________________
From: Ben
Sent: Wednesday, November 28, 2007 8:39 AM
To: Dave
Subject: RE: I can't believe it

Exactly my thoughts Dave. I had the same feeling of discontent when I purchased this, but at the same time I too am mesmerized by the slick interface. Honestly though? I have a lot invested in my iPod infrastructure. Considering both of our vehicles (Suzy’s and mine) are wired specifically for it. I’ve got cables that I’ve purchased specifically for it. We even have one of those speaker things that has a dock right on it – would be useless on another player. My iPod momentum is like an unstoppable freight train – and switching now would just be too painful. Besides, there aren’t any other players on the market with 160GB’s of space. So for now, I guess I will continue to be a loyal customer. But if this thing ever breaks, you better believe I’m going to weigh my options and start looking seriously at that Zune, or whatever else is hot at the time….

_____________________________________________
From: Dave
Sent: Wednesday, November 28, 2007 8:43 AM
To: Ben
Subject: RE: I can't believe it

Yeah, I’m with ya. It’s in my car too, and my home stereo, and I still flat-out love the thing. Even with its DRM and “you can’t have your own music back off me” attitude, I still can’t quite hate it.

But seriously, iTunes was adding songs for four hours. I have to conclude that it was just effing with me. Four hours later and not a single file on the device. What a waste of my time. Mostly, I blame iTunes… the ‘Pod wouldn’t “eat” those songs… iTunes either never put them on, or simultaneously added and then corrupted them as it went. Stupid iTunes.

_____________________________________________
From: Ben
Sent: Wednesday, November 28, 2007 8:39 AM
To: Dave
Subject: RE: I can't believe it

Dude… four hours is nothing. It took a full 8+ hours to transfer my tunes across my wireless network from my linux box to my laptop (which has iTunes installed) and subsequently to my iPod. I’m glad that worked the first time. And I was actually surprised that iTunes allowed me to use a networked drive.

That dang iPod. Hard to hate it.

Goodnight.

Work made me mad in the morning, Sharaun made me mad at lunch, and work continued to make me mad after lunch. The sun broke through on two occasions: First, the hour I had with Keaton while Sharaun was at the gym. She sat on my lap for nearly the whole time and we played. She was super huggy and talkative. Second, being able to do some brief listening to the Sgt. Pepper's Lonely Hearts Club Band multitracks on my new iPod. I wrote about them before, over here, but getting some time to actually hear them closely makes them seem so much more awesome. They are indeed amazing. I'd recommend you check them out, if you can manage to locate them, that is...

Anyway, it was a long, stressful, and frustrating day. But, I eventually made up with work... choosing to be the bigger man and continue to accept my paycheck in return for the occasional abuse. Incidentally, I also made up with Sharaun... apologizing for yelling at her and stomping around the house in a fit. So, all's well that ends well, I suppose.

But... this does not end well. Not by a long shot. Later on, at night, I decided to try out a program I've heard other audiophiles praise. It's called MediaMonkey and it's one-stop music management application, and can even sync with iPods and other portable devices. On a whim, I decided to install it. Unknowingly, I had my brand new iPod Classic plugged in when I installed and launched it. Turns out, the damn piece of software "automatically" sought out my iPod, read the contents, and somehow completely corrupted the iTunesDB file. So, when I fired up iTunes again, I got the familiar heartbreaking message: "iTunes cannot read the contents of iPod..." Sigh, all my music lost. What a waste... I'm so upset. Why can't I just learn to leave well enough alone?

Right now I'm frantically trying all sorts of recovery methods... and, even as I write this, I'm using a promising piece of software that touts one-click iPod-to-iPod cloning, with support for all generation iPods, including Classic/Touch. The cool thing is, it supposedly also will transfer all the iTunes/library data like "played count," "rating," etc. - which is exactly what I was looking for in the first place. If this works, I'll make a quick writeup and post tomorrow. Wish me luck, OK?

Really sorry about all the iPod talk, but, as if you couldn't tell, I'm a bit obsessed with this new toy. Hope you'll understand as I continue to fawn over it. Thanks for sticking it out. Goodnight.

Walking through the airport today, I had a thought: What if I was stopped, just as I was at that moment, and asked to take a detailed for-insurance-purposes-like monetary inventory of the goods I was carrying. Naturally, I started ticking off items in my head. Laptop, two iPods (not typical, but I had them both on this trip), cash, clothes, miscellaneous electronic accessories, gold rings, and the clothes I was wearing. Doing some mental arithmetic, always off by bit at best when I'm the mentalist, I was surprised to come up with a total in the several thousands of dollars. To think that people like me are so blessed that, at any given time, they have thousands of dollars of goods on their person, while there are people in the world who won't go through that in their lifetime. Not that thousands would necessarily make those folks any more happy, it's just pretty amazing the amount of material "wealth" we have with us in general. I complain because my laptop bag is heavy and uncomfortable to carry around when it's got two iPods, a book, my $200 headphones, and a couple AC adapters in it. Guess I should be thankful I'm not on my barefoot way back from the river with a yoke across my neck, two buckets of water hanging from each end.

Let's change gears now, and talk about iPods again...

I have so much room now, with my new Classic, that I'm having a great time decided what "new" things I can put on my iPod. I'd basically topped off my 60GB with what I thought was pretty much the best limited-to-60GB collection of tunes I could muster. But now, I can expand that collection more than 100%. Worried that I'll end up putting some "just OK" stuff on there, and potentially pepper the "Shuffle All" feature with bad tracks, I made myself a promise that I'll prune and manage the quality of the the new device just as diligently as I did on the old one. For starters, I'm going to load the thing up with Beatles bootlegs. Having nearly 32GB of Beatlegs in my collection, I had decided to leave them off the old iPod altogether. But, I've always wished I had at least a sampling loaded, as I feel like I now under-listen to what used to be a super-important kind class of albums to me. Problem is, I need to be careful about how I treat Beatles bootlegs, and for that matter, bootleg recordings in general, on the iPod. Because I have so many, I want to make sure that, between the Beatles' commercial and bootleg releases, my iPod doesn't get skewed too heavily to the Beatles. So, I'll do this intelligently.

1. Modify the "genre" tag (the MP3's ID3 tag) for all my Beatleg albums, making it read "Beatles bootleg"
2. Using iTunes, sort the music on my iPod by genre, and make sure that all items in the "Beatles bootleg" genre are marked as "Skip when shuffling"
3. Finally, in case I want to hear a shuffled mix of bootleg Beatles recordings, create a smart playlist which randomly grabs all songs in the "Beatles bootleg" genre
4. Ta-da! I can now put thousands of illicit Beatles tracks on my 'Pod, and not have to worry about overdosing on them during a "Shuffle Songs"

Well, sorry about all the iPod-themed entries of late... as you can see I'm having a little bit too good of a time configuring my new 160GB iPod Classic. You'll forgive me, won't you?

Thanks, and, see you back here Monday!

Being in Oregon - the land of no sales tax - I decided there was no better time than now to go ahead and drop the dosh on one of those new-fangled iPod "Classics." The 160GB-ness of the thing has been taunting me since the things were announced, and I knew it was just a matter of time before I upgraded. And, not only did I save the ~$25 sales tax I would've paid in California, but I also took advantage of the Costco price, which is already $10 less than Apple's suggested retail price (iPod's are rarely sold under this suggested price, especially by major retailers). So, all in all, I think I made out just about as good as can be. Took the thing home for $339 out the door. May sound expensive to those who could care less about 60GB vs. 160GB, but for musicophiles with platter-busting collections it really is worth it to carry around that much more variety.

So, last night I began trying to figure out just how in the world I was going to get all my music off my old iPod, and subsequently on to my new iPod. See, I manually manage my music on my iPod - I don't use the iTunes library features to manage my music collection, and that means I also don't use the "automatically sync" feature to get music on and off my device.

I realize this may put me in a minority of users, but, because 1) I don't use iTunes to manage my music in general, and 2) my collection is larger than my iPod's capacity, it's just more convenient for me to drag-and-drop what I want when I want rather than relying on some selective sync functionality. Don't get me wrong, I can see the plus-side to using the auto-sync functionality, like not having to completely delete and re-add things in situations where I've "updated" an MP3 folder/album on my hard drive, perhaps adding artwork or updating ID3 tags. But still, I prefer to do it manually.

Anyway, back to my problem. Surely someone has faced this before. Say you're a manual iPod user like me (there has to be more of us out there, right?), and you outgrow your old iPod, or just figure the new one is plain "cooler," and decide to upgrade to Apple's latest offering. If you're like me, you've likely spent a lot of time pruning, tending, and shaping the music (and other content) on your iPod, and you probably want to "start" with your new iPod having the same content as your old one, and then add new content from there. In other words, it'd be nice if the "baseline" content on your new iPod was a mirror image, or snapshot, of what all is on your old iPod. Makes sense, right? Think of it as "migrating" the entirety of your old iPod onto your new one.

Note: I'm aware that techniques exist for doing this using both iPods in disk mode, but I'm pretty sure that will only work on two iPod's of the same generation (or, at the least, having the same database version). Since Apple changed the iTunesDB structure completely (version 25) going to the Touch/Classic sixth generation devices, I don't think I can get away with doing something as easy as this when moving from a less-than-sixth generation one. But, honestly, I also didn't give it a try.

Again, before you criticize me in the comments and tell me this would all be "easy as pie" if I just used iTunes to manage my music collection - I know. Trust me, I know. I just don't want to use iTunes to manage my music, OK? Now that we're done with that...

Now, even though I still have all the content that's on my iPod stored on my PC, I don't exactly know offhand what's on there and what's not. I have a general idea, but my collection is huuuge, and the best and easiest way to be sure I get an exact copy of my existing iPod content would be to simply "copy off" everything that's on there and then move it to my new iPod. Sure, worst case, I could simply re-pick all the right content from my larger collection, but it would likely take me weeks to get just the right items (honestly, you may opt to do this... give yourself a "fresh start" and relive the fun that is filling your iPod with the perfect collection of music for the first time). So, again, we need to do the following things:

• Copy all the music off my old iPod (and onto the PC, as an intermediary location)
• Put the resulting music from step one onto the new iPod, ideally retaining the neat track-level metadata like "last played" dates, ratings, play count, etc.

I'm gonna tell you how I did this, even though it was an imperfect process in the end (meaning, I didn't exactly meet my own requirements above, as I lost the iTunes/iPod metadata). Ready? Here it is; it's actually quite simple:

1. Download SharePod and copy the folder to your old iPod (your iPod must be plugged in, and must be enabled for "disk mode" use).
2. Run SharePod from your old iPod (if you get an error, make sure you have the .NET framework installed).
3. Select all your songs from SharePod's righthand pane, and click the "Copy to PC" button.
4. Choose your preferred location and foldername/filename structure (make sure you have enough hard drive space to hold what you plan to copy off).
5. Kick back and relax while SharePod copies every last track off your iPod (if you had a full 60GB model like I did, this can take over an hour, even at USB2.0 speeds).
6. After SharePod is done, close it out and unplug your old iPod.
7. Plug in your new iPod.
8. Fire up iTunes (or, alternately, fire up whatever you normally use to add songs to your iPod), and drop all the extracted tunes on your new iPod.
9. Relax while iTunes (or whatever you use) copies all your songs onto your new device.
10. Oh, and remember, if SharePod saved the day for you... go ahead and PayPal the author a few bucks... it was certainly worth it for me!

To be clear, SharePod does create an XML file which you can use via iTunes' "Import" function. I originally thought that, since this XML file contained the metadata mentioned above, I may be able to preserve things like "play count" and rating, etc. when importing. Turns out, iTunes didn't "get" the metadata, even when using the import feature and SharePod's XML file (at least, for me it didn't). So, the end result is that you'll effectively reset all that data. You'll lose play counts, ratings, last played dates, etc. It kinda sucks, but it's better than nothing. And, as far as I was willing to muck with it, it was the best I could come up with.

There may be other ways to do this, using different software to achieve the same thing (especially since I'm only talking Windows here, and not Mac). But I think it all amounts to the simple process of 1) extracting the data from the old device and 2) putting back on the new device. I would love to find a way to maintain the metadata (I know... you're going to say, "Use iTunes to manage your music..."), but for now I'm happy enough to have a cloned copy of my old iPod as a starting-point for my new one.

But Dave, what about my playlists?

Look, I know that a lot of people have spent a big amount of time and effort making super-awesome playlists from the content on their iPods. For that reason, I can see why you'd want to make sure your playlists come over to your new iPod intact as well. Unfortunately, I'm not entirely sure how to do this, as I didn't have any treasured playlists I wanted to bring over for my upgrade. I think, however, that you can use SharePod's playlist export feature in much the same way as described above for tracks to accomplish the same thing. Export the playlist, which, I believe, amounts to exporting the songs that the playlist contains, and then import the playlist through iTunes using the XML file that SharePod creates.

Well, that's it. That's I how managed to transfer all the music from my old iPod onto my new iPod, and start with what's essentially a carbon-copy of what I already had. Hope it helps someone who may find themselves wanting to do the same thing. Oh, and, by the way, if anyone has any suggestions or tweaks for this process (especially if you know how to do the above while keeping the metadata for the tracks), please leave a comment on this entry and let the world know! Thanks!

Update - 11.27.07

After writing this, I decided to try a bunch of commercially available alternatives to the method I describe above. For what it’s worth, all the software I tried was able to get the MP3s off the device. However, none were able to successfully preserve the iTunes metadata (things like playcounts, preset-EQ, date-added, skipcounts, etc.). My findings:

• CopyTrans: This application is supposed to copy music from your iPod and into your iTunes library. The webpage advertises full iPod Classic compatibility. Out of the four, CopyTrans got closest to what I want as it was able to import the playcount and date-added metadata into iTunes.
• iCloner : Part of the CopyTrans suite, this is like Ghost for iPods. It promises to make a “clone” backup of one iPod which can be restored onto another iPod. The functionality is there: I “cloned” my 5G iPod and then restored the image onto my new 6G iPod. However, the 6G with the restored 5G image was still unrecognizable to iTunes, and the music would not play. I also noticed that, in disk view, the post-restoration 6G iPod was truly a “clone” of the 5G (which is a bad thing, since Apple changed the folder and database structure from 5th to 6th generation). Even though the website claims full iPod Classic compatibility, the version of iCloner I used couldn’t do 5G-to-6G. Interestingly, I have to think that iCloner may indeed be a “real” solution to my problem if I was trying to move from one same-generation iPod to another. And even though I haven’t tested it, I would expect iCloner to make a carbon-copy, including all meta-data, if the target iPod is of the same generation as the source.
• Music Rescue (formerly PodUtil): Music Rescue also successfully exported the raw MP3 files, but was unable to preserve the metadata when importing the tracks iTunes.
• Amarok (Linux only): Although I didn’t run the test myself, I had a Ubuntu-loving buddy confirm that the latest version of Amorak (at the time of writing, at least) can export MP3s from iPods (all generations), and copy them back onto iPods (all generations). However, when testing specifically to see if the metadata can be preserved, nothing was imported.
• iTSfv (iTunes Store File Validator): This tiny piece of free and versatile software can do lots of neat things with your iTunes music library, and has an extremely promising tab called “Backup/Restore.” At first glance, this tab appears to contain the holy grail: The ability to export an XML file containing only the not-in-ID3 metadata for your tracks, along with another option to “restore” the data in the resulting XML file back “over top” of another library (iTSfv looks for matching song titles, and writes the saved metadata on a hit). Unfortunately, it looks like iTSfv can only export this data from tracks that already “live” in an established iTunes library, and not directly off of an iPod. Too bad, because it looks nearly perfect for what I want. However, being that iTSfv is open-source, I’m actually tinkering with the idea of modifying it to work directly off the iPod… keep your fingers crossed.

So, again, overall it seems like there are a lot of solutions to reclaim your actual MP3 files from an iPod and move them to a new one (regardless of iPod generation). However, based on my research, I cannot find any reliable application to reclaim files and metadata – specifically going from a pre-6G device to a 6G one. So all you people who manually manage your music, and want to upgrade your iPod Photo to an iPod Classic… get ready to lose your metadata.

Again, commentary welcome!

Oh, and hey, before I go... and also iPod related...

On another note, I'm with this poster... I'd love it if Apple allowed you to group the tracks within a playlist by album or artist. This way, you could open a "New Music" playlist and see, not a huge list of songs, but instead, a nice tidy list organized albums or artists, to which you could further drill-down to track level. I know this isn't useful for most folks who don't view their music from an album-level of granularity (rather than just a "loose" collection of tracks), but since I tend to listen to music as albums moreso than a string of singles - it would indeed be useful to me. Anyway, would be nice to see in a future firmware... is all I'm sayin'.

Until later, take care.