Strange error when trying to sync video and cannot get past HELP!

My Ipod (and I have another one as well, a photo that works just fine with everything) will simply not sync all the way. It works until it encounters an error, and then quits. This ipod, a 60 gig video does this as well as another ipod I have, a 30 gig video. Yes I have 3 ipods, its crazy.
It happends EVERY time it gets to 30 days, Immigaration. I have tried not syncing it but it still happens again later, some of the videos will download though.
The error message is:
These are regular videos that I bought through ITUNES.
PLEASE HELP!!!
dell 9300   Windows XP  

I can't recall ever seeing an error -93. These are two of the most common.
Error -36, disk cannot be read from or written to error syncing iPod in iTunes.
iTunes displays error 69 when syncing iPod.
"It happends EVERY time it gets to 30 days, Immigaration."
Could you explain what you mean by this.

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