Fordoix -
Good news - I was able to recover allocated and deleted files from the copy of my iPod drive and these files played in Windows Media Player and iTunes. All the info (Artist, Album, etc) was still present for each recovered file. For purchased music, iTunes prompted me for the password to authenticate the computer.
Bad news - The software and technology I'm using is the same stuff that corporate security and law enforcement use in computer investigations. The computer I'm using is designed for computer forensics and the software is expensive ($2500).
More bad news - It would be difficult for you to replicate what I am doing. However, if you want to give it a try, here's what I did. I connected my iPod to a write protected firewire port on my forensic computer. I then created a sector by sector copy of the iPod's drive to a separate hard drive in the forensic box. I examined that copy with a forensic analysis tool (EnCase
www.encase.com) and carved out some MP3 and M4P files to the forensic computer's hard drive. Those files could then be burned to a disc, loaded into iTunes, or whatever as they are now just files. For you to do this, you would need software to make the copy of the iPod and software to examine the copy for the music files. It doesn't have to be what I used but it will probably be more than the software listed here since most/all of those examine the iPod live and unprotected. This is something we never do in computer forensics. Also, there's no guarantee that this will work for you. If the files on the iPod are corrupted for whatever reason, then its unlikely that anything will bring them back. But its always worth a try.
Maybe good news - Check your PM for my contact info. Maybe we can work this out to try to get some/all of your files back.
Tony