Having trouble syncing TV shows to iPod

I get the error "Cannot sync iPod because the required disk cannot be found". It's not a space issue because I'm only trying to sync about 5 episodes of Lost. I have 7.41ish GB left of space while all episodes take 11ish GB.
Even if I try to manually sync it, I always get this same errors. I tried to restore my iPod and an error occured that wouldn't let me. Any ideas on what's going on?

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