Plenty of ipod space, but iTunes says I can't update or synchronize

I can't synchronize my ipod and itunes library. When I select my playlists and apply, I get a "Can't update because there's not enough space on your ipod". There aren't any files on the ipod though.

Restore the iPod.
tried it once, will do it again. I had to restore my
library after my hard drive crashed. Would this have
any effect??
Well, I'm on my third restore and now I'm ******. Also seems to be trying to load podcasts on the ipod by default. Unchecked the synch button on podcast, but it still tells me I don't have enough space.

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