All of that rubbish!
The problem is not with connection but I believe with your HDD on iPod.
I have the same problem and tried many different things.
1. That's not songs fault - cos when formatted iPod and restored the disk I copied songs that was "broken" before and have no problem.
2. When get to the point where I believe I have bad sectors on iPod's HDD none of songs can be copied. I have Error 69 all the time.
Solution: (might temporary but works!!!!!)
I messed up a bit cos formatted iPod's HDD for FAT16 then had problem to restore to FAT32 but managed!!
1. Go to disk mode:
- RESET iPod(menu+centre buttons), just after reseting
- DISK MODE (centre+play/pause buttons).
2. While in disk mode format it from DOS or (as colled in new Win) COMMAND PROMPT. Can be quick or full format. My iPod was seen as disk F: so:
format f: FS:FAT32 /Q (Q is quick but full is better)
3. RESET iPod.
4. Restore in iTunes!
Works for me!
Will update if anythong change.
Any questions :Email Id removed for security