Hey guys,
I started my own thread on same/similar problem, and have chimed in on other threads about this too...I am using the latest version of Itunes and Firmware 1.1.2 on a new Ipod Classic 80gb. I'm a longtime user of a 5g Ipod, and had problems syncing with my old library. My new Ipod Classic would often freeze during a sync, I would have to prematurely disconnect my Ipod, which would lead to a blank Ipod, and then I would have to perform a Restore and start over.
The way I have got things stable/working again, is to delete your entire Itunes database folder (located in My Documents > My Music). Though I did keep my Artwork Folder. And then, start your library from scratch. I know this *****, but basically, for me, my Itunes Database files got corrupted.
It looks like we are all windows users here too.