YtseBitsySpider, I had the same problem and this definitely fixed it:
The problem is with your HDD on iPod.
1. It's not the songs fault - when the iPod is formatted and the disk restored, the songs that once were broken or with errors are now suddenly fixed.
Solution:
1. Go to disk mode (plugged in in your pc):
- RESET iPod (menu+center buttons), immediately while it is reseting
- DISK MODE (centre+play/pause buttons).
2. While in disk mode full format it from DOS (COMMAND PROMPT; just type cmd in the start menu, click enter). My iPod was seen as disk F: -it can be g: as well or any letter it assigns to your iPod- so:
format f: FS:FAT32 /Q (Q is quick but F (/F) Full is what you need). This may take a while, like an hour or thirty minutes. Be patient.
3. Reassign the name of your (iPod's) Hard Drive (F:, G:, ...)
4. RESET iPod (menu + center).
5. Restore in iTunes