My roomate in college had the same problem. I believe he used the free version of CopyTrans or iRip which was limited to like 10 songs at a time or something rediculus like that. He painstakingly made it work without purchasing the program, though it took a very long time. Have you tried a google search of "copy songs from iPod?" There seem to be many program/app suggestions out there.Here
is a quick google hit to try out.
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