New Ipod Nano 3rd Gen. Won't Sync Properly

I iPod Nano 3rd generation and, every time I plug it in and click "Sync", about midway through completion, I will recieve this message:
"Attempting to copy “DANIEL’S IP” failed. An unknown error occurred (-69)."
I don't even know what Daniel's IP is, let alone understand why it does this. I recently tried syncing my music to an iPod Nano 2nd Gen. 4GB and it got through the letter "J" (Artist name) and gave me this message. I bought this new 3rd Gen. Nano and it, too, only goes through letter "J" and gives me this message. PLEASE HELP!

No, I was hoping no one would say that. It is not a bad file because, on my nano 2nd gen 8 GB, every song was transferred. Plus, it stops at a different song each time and I have watched the top and still couldn't find where it stops. My question is still unanswered.

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