WON'T FINISH Syncing . (error -48)or 1033, -69

Itunes WON'T FINISH SYNCING. (error -48)or 1033, -69. It hangs up on a new song each attempt. I have deleted the sticking song each failure.
Here's what I've tried:
A) unchecked all Recently added songs and delted skipped disc tracks, as well as
those mp3's brought over via drag n drop.
1) updated Itunes, restored Ipod 14 times.
2) restored ipod from PC/Itunes 12 times.
3) updated USB drivers and uninstalled and reinstalled
4) ran MS disk scan /repair 15 times.
5) tried all 4 USB ports
6) ran diagnostics and it said it couldn't find Ipod, (although in itunes margin it showed Ipod). I clicked HELP and it took me to an apple support page that had nothing to do with my particular error/ diagnositc result. OF COURSE , THAT WOULD BE TOO LOGICAL!
Diagnostics should trouble shoot this until it's fixed. No such process.
Any help?

Bump. I am having this problem also on my 160 GB Ipod. I have restored a ton of times and have use multiple computers to load songs from (thank God for my EXT. HD) If any one can help i would greatly appreciate it. Thank You.

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