there are programs available to help you do this if you want (my legitimate reason was trying to consolidate all the music from our Mac and our PC onto one iPod )
A search on google should turn up a program that will help you accomplish this. I'm not going to point you in a more specific direction that that in case your reasons are not as legitimate as mine were
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I needed to move all of my music from my crashing desktop to my new laptop. The only cheap and effective way is to enable diskuse via iTunes/ iPod and copy files from my old comp to my iPod. After doing that I needed a way to move my music there are plenty of free or cheap programs out there to do that. I just used www.yamipod.com it works ok but crashed halfway through, it may be buggy so use at your own risk.
Ipod Viewer is a program that can help you to move items back to your computer via the ipod. Unless you INTENTIALLY are trying to take copyrighted material off of another ipod and stick it onto your computer, moving these items back and forth is, I believe, completely legal. I do this all the time as I have imacs at work and at home. There may be better programs out now, but it was available online and has worked well for me. It was also mentioned in the "Missing Manual Ipod/Itunes" book.