iPod Sync Issue

Hello,
When i recently switched to Mac, i was busy getting it setup with the software and files that i need and forgot to update my iPod. When i recently plugged in my iPod, it uploaded, and then froze half way thru.
I tried this a few times, and it brings the same results.

What do you think i should do?

if you have all of the songs/pictures/videos that are on your ipod on your macbook..

i would plug in the ipod and restore it using ipod updater. then plug it back in and try to sync it with itunes again.