Well. In hindsight I should have taken the appearance of random artwork on my Animatrix songs as a sign of bad things to come. It is only recently I had decided to google the album name of the cover and discovered it had no relation to any song on the Animatrix soundtrack. At all. So clearly something was going wrong months ago, I was just too stupid to catch it.
Now, the basic way to fix such issues is to disable artwork on your iPod, wait for the iPod to update, then re-enable. However, it was during this re-enabling process that I would get a (-50) error. Now only some of the albums were showing any art, but most of them were blank. Basically the only solutions I found were “use a different cable” and “do a restore”. Since I couldn’t find my old cable, I was basically left with the latter. This did not make me happy, since Apple in all its glory took out the ability to take songs off your iPod and onto your hard drive easily.
Backing up the music wasn’t hard for me, just annoying, and the restore is just a one click process. Reimporting all that music (I had about 5.36GB) was the long part; not so much getting the files into the library, as deleting all the duplicates-because again, Apple didn’t see fit to have such a feature built in.
But yay, the iPod is working properly again. Today, I spent a good portion actually going through the albums that never had any artwork to begin with and tried to fix that. In some cases I had to actually make my own (like for mixes, or what-have-you). I really wish you could do the Find Album Art thing on your iPod.
And yes I am anal about the cover art, because it’s silly to have a fancy iPod with coverflow, if you don’t have covers!