ipod classic not syncing past 2 songs

I was having the same problem.

I have an i pod classic 80GB (with the wheel) I think it's 5th generation

I would start a Sync, it would sync 2 or 3 songs then stop or hang up, which did not interfere with any other function, so I would not say it froze.

Once I ended the sync by clicking on the X next to the sync progress bar at the top of the window, I ejected the ipod and then plugged it in again. Then I selected my i pod under Devices in the menu on the left-hand side of iTunes. Clicked on the summary tag. Clicked on "Manually manage music and videos" Clicked ok and apply.

When in manual mode, you cn drag songs from iTunes to the device icon in the sidebar. Once I downloaded the song or songs or album that was causing the problem, I then unselected manual load, and everything else was able to sync normally on automatic mode.

I have the same problem after the initial sync (which is usually about 4,000 songs). I'm running Windows 7 , but everything else is the same. I know I can manually add all the songs, but I didn't pay all this money for an iPod to have it 'kinda" work. I have been experiencing this problem since I upgraded to the New iTunes. I have an extensive library and its a waste of money to have my iPod at 10% capacity.

Another potential workaround (but still a pain) is to uncheck all songs and then check about 300 at a time. iTunes/iPod Classic seems to accept "batch" deliveries of this kind but won't sync the whole list at once. Worth a try if you are patient.

Actually I have found you can sync up to at least 4,000 songs at a time by this method.