Ipod Classic crashes Itunes when trying to sync

Recently I have been trying to sync my Ipod Classic to put some new songs on it, however when I try to, my ipod crashes on the 'Determining Tracks to Sync' step. I have tried selecting only the new songs for the Ipod to sync, 1 at a time even, but still crashes on that step. (Left me with only 2 songs on my Ipod..somehow). I can play any of the songs I own perfectly fine in Itunes as well.

I'm running Windows XP, Itunes version 11.1.0.12 , and have tried every USB port on my computer, always the same problem.

The exact error is:

"Windows - Device Timeout
The specified I/O operation on \Device\Harddisk5\DR10 was not completed before the time-out period expired."

Also occasionally this:
"The iPod "Ben's iPod" cannot be synced. An unknown error occurred (13010)."
And this going along with that one:
"iTunes could not copy "SONGNAME" to the iPod "Ben's iPod" because an unknown error occurred (-50)."

If it helps out any at all, here is the Hard Drive data

• Retracts: 2
• Reallocs: 480
• Pending Sectors: 280
• PowerOn Hours: 207
• Starts/Stops: 28717
• Temp: Current 22 C
• Temp: Min 14 C
• Temp: Max 54C

The reallocs, and pending sectors are high yes, but this had never been a problem before when trying to sync.

I haven't tried it on another computer as I don't have another computer to try it on.

Would appreciate any help, thanks.