that 16GB in "other" makes me wonder, it sounds unusually big... perhaps you have something in your iTunes library on your Mac (or PC?) which is causing the problem? perhaps a corrupted file... maybe when iTunes gets to syncing that corrupted file it croaks.
here's what I would try
- create a new user with an empty iTunes library (or just a few MB of songs) and try syncing under that user. see if sync still stops.
- if that works re-import some or all of your songs into this new user's iTune library, then try syncing again with this now larger library.
- back under your user, with your original iTunes library, open up Console (I'm assuming your on a Mac...) then sync and see if there are any error messages in the Console that might give a hint. if you're on a PC, I'm not sure if you can get a similar error log like in Console.
are you using iTunes 9? and do you have music or videos you have purchased from the iTunes store? if so, another thing to try is to go into iTunes, then under the Store menu, Deauthorize your computer, then re- Authorize it again after that. there are reports that this fixes some people's problems syncing with iTunes 9.