Unless you have access to your friends original MP3's on a seperate hard file its a waste of time. If you try and repatriate from one ipod to another the sound is so crap. Ipod is the hardest device to get around on this issue and they are successful on it too. Digitial download songs have certficates on them that only allow 3 transfers etc. Album purchases are cheaper and are easier to manage transfers onto other devices.
Michael, just curious - would you like to clarify why the sound would be
crap, if you use either the manual method posted below or one of the utilities to copy iPod MP3s back onto your hard drive?
Or are you referring to the analogue connection hole (covered below)?
Apple probably don't support moving libraries from an iPod to your PC/Mac directly as they feel it will encourage music sharing and that people will sell their second hand iPods full with music etc.
Note that Apple now allow you to recover iTunes Store purchases that are on your iPod but have got lost or are no longer in your iTunes music library.
There are probably not that many "legitimate" reasons why someone would lose access to their "master" iTunes music library (without a backup) and need to get the files back from their iPod.
However, the software solutions mentioned above will work reasonably well in this case.
In terms of iTunes Store downloads and DRM, not that the entire EMI catalogue is available at higher bitrate and DRM-free, hopefully, this will become the norm. Note also that it is not Apple who insist on DRM but the music companies themselves.
Finally, when you say "album purchases are easy to manage", what do you mean? If you mean CDs purchased, then I agree.