My son had his computer hard drive crash and all of his songs in iTunes disappeared. He thought he was saved as he had them all on his iPod, but when he tried to download them to his formatted new hard disk using iTunes he could not.
iTunes will not download music from an iPod back to a PC. Man, he was bummed. Tons and tons of songs all gone except in his car where he connects his iPod. No more listening to his music at home from his PC.
I checked online for a solution to help him out and found a great one. It is called Pod to PC. On top of a cool application that solved the problem, it is free!
The solution in his case was to install the PodtoPC software on his computer, connect his iPod and the software imported all of his songs found on his iPod down to his PC with one click. The program will even synch songs and can be used to load songs to your iPod. There is even a version for Macs called Pod To Mac. The program works within iTunes so you don’t need to have another music archiving system. Why Apple didn’t do this in the first place I don’t know, but the solution, when you need it is elegant – easy to use and free.