IPod Won't Finish Sync

So, today I've had to restore my iPod to factory settings about our times now. Every time I try to re-sync all my music back, it'll slow down significantly and stop around after 1700 songs or so (out of roughly 3700). When I try to eject my iPod, iTunes crashes and the files already copied do not show up on my iPod. When I reconnect to my MacBook, it shows everything I copied as "Other" and not "Music." I've tried this several times already and it still won't work.
EDIT: Make that five restores tonight.
Message was edited by: Evan Wohrman

So now I've also tried connecting it to my Windows PC and restoring it, and iTunes does the exact same thing. It locks up on one song and never finishes the sync, and crashes when I try to eject.
My iPod didn't start doing this until yesterday.

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Try:
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IPod Won't Finish Sync

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