IPod only updating 36 out of 197 purchased items...

I only have one iTunes account authorized to my computer and iPod. Mine. I have purchased 197 songs over the lifetime of said account, and my iPod will only sync 36 of them. I haven't been able to determine any pattern. I've tried all the obvious (song length, purchase date, play count, last played, genre, etc.)
I called iTunes customer support and they had no idea. They told me to call iPod support (which would cost me a bunch of money, as I'm not under warranty).
I've tried reauthorizing, restoring my iPod (can't, get an error: 1418), I've deleted my SC folder innumerable times, reinstalled iTunes, making sure the sync settings were applied properly (Sync All Music And Playlists), made sure I have plenty of space left on my iPod, etc.
Any ideas?
Thanks for any input!
-Alias

Well, first of all, they are all checked; secondly, I don't have the box saying "sync only checked songs and videos" checked, so either way, that's not the problem.
Thanks, though.
-Alias

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