ITunes freezes when I try to sync iPod

I have a 80GB iPod Classic and I just recently switched from a PC to Mac. Ever since the switch I haven't been able to sync with my iTunes library. I plug the iPod in, it recognizes it, begins syncing, and after 50 or so songs everything freezes. At this point all I can do is unplug the iPod (which I know is bad for it, but I have no other option - I've tried waiting several hours and it doesn't unfreeze).
During one of my attempts, I was able to update my iPod software and re-format it to Mac, so I know that is not the problem. I have tried resetting my iPod as well.
Thanks in advance

I have always had this iPod with Mac, but having the same exact problem. It seems others are too, but nobody has any suggestions. Apple doesn't seem to offer any updates or patches even though i've reported this problem at least 20 times. Guess we're screwed.

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