Plaidophile

This is how you can narrow down which file(s) in your archive may be causing your 5th-generation iPod (with video playback) to fail to boot (or, more accurately, start to boot up but then not get past the Apple logo, and then start over again).

First, when your iPod gets stuck in a reboot loop, hold down the center button and play button until it goes into Disk Mode. In iTunes, create two playlists, one called "break test" and one called "break candidate." Drag the contents of your currently-syncing playlist(s) (or your library, if applicable), including any podcasts you may be subscribed to, into "break candidate" (this requires that you are syncing with playlists or the whole library, obviously; if you're manually managing your iPod, this won't quite work for you). Set the iPod to sync ONLY the "break test" playlist.

Next, do the following steps, in order:

1. Go to the "break candidate" playlist, and select the first half of the files (click on the first one, scroll halfway down, then shift-click on the middle one; you don't have to be exact or anything though)
2. Drag the selected playlist entries into the "break test" playlist, and then delete them from the "break candidate" playlist
3. Update the iPod, and wait for it to finish
4. On the iPod, hold down the center and menu keys for 5 seconds to make the iPod reboot
5. If the iPod fails to boot:
   • Move the first half of the files from the "break test" playlist into the "break candidate" playlist (i.e. drag them to "break candidate" and then delete them from "break test")
   • If there are only a few songs left in "break test," go through them to see if there's any weird characters in the song info. If so, edit the song info and fix it.
   • Hold down center/play to put the iPod into disk mode
   • When the iPod finishes syncing, hold down center/menu to reset it
   • Repeat the above four instructions until the iPod boots
6. Great, now you've ensured that everything in the "break test" playlist is fine, so clear out that playlist (select-all, then delete), and then start from step 1 above. Repeat until both "break test" and "break candidate" are empty.

This process is pretty tedious, but it's a lot less tedious than going through each file individually, as long as there's more good files than bad files. If there's at least as many bad files as good files, it's better to just move files 10-20 or so at a time from "break candidate" to "break test."

Even better would be if Apple didn't leave this horrible bug in the iPod to begin with, though. Not all mp3s are tagged in UTF-8!