Can't you just sync it with iTunes?
(I'm not sure myself, but I would try that first)
No, if he tried that he'd end up with a blank Ipod.
You using a Mac or *spits* PC ?
Tried that and it wanted to wipe it itself :SWhat did you type into Google?
http://www.mp3buzz.net/index.php/2006/06/03/ask-the-buzz-how-to-get-my-music-off-my-ipod-2/