Can't sync music on 3rd gen ipod touch

I recently recieved a new laptop running windows 8.1 and at least three quarters of my music downloads will not sync to my ipod. I keep getting anywhere from file cannot be converted to unknown error has occurred. Yes some of these were downloaded from file sharing sites and some where purchased from apple themselves.

Do the songs play in iTunes on the computer?
Have you restored the iPod on this computer?
You have to since you can only sync with one computer.
What is the for mat of the songs?
What are the complete wording of the  other error messages?

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