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.
Main: i5-3570K, ASRock Z77 Pro4-M, MSI RX480 8G, 500GB Crucial BX100, 2 TB Samsung EcoGreen F4, 16GB 1600MHz G.Skill @1.25V, EVGA 550-G2, Silverstone PS07B
HTPC: A8-5600K, MSI FM2-A75IA-E53, 4TB Seagate SSHD, 8GB 1866MHz G.Skill, Crosley D-25 Case Mod