Another iPod Bug:
I can't seem to get anything in the iPod's database. I.e. when I sync the iPod with MC, songs will be added to the player's harddrive, however they won't show up on the iPod itself. In MC it says unsupported file-format or something similar when I look at the content of the iPod.
I've tried initializing the iPod as well as reformatting it with the iPod software but I still won't work.
Hope you fix it soon.
I don't really have a solution (would've suggested reinitializing, but you've already done that) -- but, I saw the same thing you did in MC -- namely that the iPod window in MC said a bunch of files had "unsupported file format". In my case, all those files were .mp4 files from iTunes. However, those songs DID transfer and they DO play on the iPod.
So there is some bug in what MC shows in the iPod window, but in my case, it didn't interfere with the correct actions happening.