So, I've tried other programs to sync it - Media Monkey, Songbird - and no luck. So I restored the ipod, dumped everything off of it and tried with itunes again. It looks like as it is syncing, it is going to sync the entire library - but each and every time it gets to where there is only about 100 songs left to sync, itunes freezes and in turn completely freezes my laptop. Tried reinstalling itunes again, but same issue.
I've got a 120gb iPod Classic and running my computer on Windows Vista. Any suggestions of help would be awesome... I really miss my ipod and my laptop is taking a beating having to be restarted every single time itunes decides to have a fit.