After looking for a way to listen to my 30 GBs of music that lay on my old Starmax running 9.2 from my PowerBook G4, I came up with a quick solution. Rather than copy 30 GBs of music to my Powerbook and try to synchronize both libraries, I found a way to easily make iTunes load remote libraries as your own.
On the OS 9 side, select your iTunes folder and set up sharing permissions so that this folder is its own share point (i.e. it shows up as a separate item in the "Select Volumes You Wish To Mount" dialog). Now go to your other machine, in my case the PowerBook, connect to the OS 9 machine, and select the "iTunes" volume. Now make an alias and throw it in the Music folder in your home directory. iTunes should see it as your local files, and load up the library.
Now the problem is I'm not always able to connect to my OS 9 box and like to have some MP3s to listen to on the road. So I wrote a quick script to go in the scripting menu that allows you to seamlessly switch between local and remote libraries. To get the script to work properly you'll have to edit the paths in the code and create a folder named "Libraries" in your home Music folder with two folders inside of it, "Local" and "Remote". Local should contain your "iTunes" folder and Remote should contain the alias "iTunes" to the remote machine.
Mac OS X Hints
http://hints.macworld.com/article.php?story=2003050323231448