Won't import into ipod.. urrrghhhh

I have a bunch of songs that I downloaded, and they won't upload into my ipod. They have been changed to AAC's, so that should be ok.. I downloaded about 500 songs at once. They work fine in my itunes library, just won't upload. Ever since i put those in my library, songs that I have BOUGHT from itunes or ripped from my cd's won't upload into my ipod either. can anyone help?
PS - when I click update ipod, it says it has updated. the screen on the ipod still says do not disconnect.

I'm having the same problem. Bought a 30GB video ipod...at first it all worked, did the update for the ipod and itunes....all of a sudden, everything went wrong. Had to uninstall, reinstall, restored the ipod, and now the only music i can put on my ipod are ones that i've ripped from my cd's, anything that i've bought from the music store won't work for some reason. They play in itunes but won't upload into itunes. And when I do put them into the ipod, it says "Itunes has encountered a problem and must close". Very frustrating!!! Help if you can!!! Thanks!!!

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