The fellow was a musician with his own recording studio. Obviously he knew what he was doing far better than I could follow. What you said is the way things were supposed to work. However, they didn’t for reasons I don’t recall from our casual conversation. All I can remember now at this late date is that his computer’s hard drive died on him at about the same time his Apple device malfunctioned. When he went through all of the normal procedures to put everything back to normal, the procedures did not work like they were supposed to, and Apple refused to help him, especially with respect to the files not obtained from the iTunes Store. Some of those tunes were his own compositions which had been backed up on the hard drive that failed before he recorded them to CD.
He was left with the choice of repurchasing the iTunes and losing his non-iTunes files or using a hack to reestablish access to the files on his Apple device. The hack worked, and he recovered a huge amount of files on his Apple device. he then backed them up to multiple hard drives and CDs.
You do know that none of that makes any sense at all, don't you? Something just does not sound right. Apple would certainly have assisted him in retrieving the data off of his iPod. . . I have read and seen of many times where they have done this. Hacking was also unnecessary. Merely syncing it back to a newly authorized iTunes would do it easily. I've done it for clients.
The only time I have seen Apple dig in their heels and refuse is when a person cannot prove their identity. Then they will NOT cooperate at all.