Dinobot, just to make sure you follow the Apple fix first "This error occurs when iTunes tries to send files to your iPod, but a file (or files) is unusable (something is wrong with it).
To figure out which file (or files) is causing the error, update to the latest version of iTunes and then do this:
Control-click (Mac) or right-click (Windows) on your iPod icon in the iTunes Source pane, then choose Sync Songs from the shortcut menu.
Watch the display at the top of the iTunes window while your iPod is being updated. The name of the problematic file should appear in the display right before the error appears. Then, remove the bad file from the list of songs to be synced to your iPod.
Select the iPod in the iTunes Source pane.
Click the Summary tab.
Select the "Sync only checked songs and videos" checkbox (please note that this checkbox is only available for an iPod configured to update automatically).
Select the appropriate item under Library in the sidebar, and find the bad file in the list. (For example, if the file in question was a song, you would select Music in the iTunes Source pane. If it were a video, you would select Movies or TV Shows in the sidebar.)
Deselect the checkbox next to the file name.
Repeat steps 1 and 2 to update your iPod. If you have multiple problematic files in your iTunes library, you may need to repeat the other steps to remove them too.
To prevent future issues, you should delete the unusable files from your iTunes library, then restore them from a backup, or reimport them from a CD." from here
It is also possible that there is a timing issue between the iPod and the Computer during syncing. You can try to restore your ipod, but make sure it is in disk mode. Wait for the ipod to sync, and when it starts freezing on a song, rapidly tap or hold play/pause until it starts syncing again. To place the iPod in Disk Mode "Putting iPod devices with a Click Wheel into Disk Mode
If necessary, verify that your iPod has a Click Wheel.
Before placing the iPod into Disk Mode, verify that it is charged.
Toggle the Hold switch on and off (set it to Hold, then turn it off again.)
Press and hold the Menu and Select buttons for at least six seconds, until the Apple logo appears.
When the Apple logo appears, release the Menu and Select buttons and immediately press and hold the Select and the Play/Pause buttons until the Disk Mode screen appears.
Connect the iPod to your computer; the screen on the iPod will should say "Do not disconnect".
If you are having difficulty putting your iPod into Disk Mode, set it on a flat surface. Make sure that the finger pressing the Select button is not touching the Click Wheel. Also make sure that you are pressing the Play/Pause button toward the outside of the Click Wheel and not near the center. If you are still unable to put your iPod into Disk Mode, use one finger from one hand to press the Select button, and one finger from the other hand to press the Play/Pause button. From here
Hope this helps, good luck.