Solution:

1. Setup music library as it’s own share
2. Create folder script using Automator (shout out to Elliot here), and attach it to the music folder.

Script: Get selected folder items, add songs to itunes playlist (set to library)

3. iTunes is set to keep the library organized and share the whole thing. Just drop music files anywhere in the library folder, iTunes will add them, and organize them as needed. The folder action only detects changes, so the rest of the library is ignored.

4. Just to be fancy, I have an itunes smart playlist which lists all of the songs added in the past 30 days.

so far, so good!

I use both SlimServer and Daapleganger for my iTunes-based music server.

Get Specified Finder Items (Finder) > Import Audio File (iTunes)

Be sure to check the “Delete source files after encoding” option (unless you’re sharing the folder with a friend). Then save as a Plug In for Folder Actions, and attach to the folder of your choosing.

If you and the friend both have access to the same sharepoint, and you both attach that folder action to the folder, it will act like a drop point for music for both of your iTunes libraries. Put a file in, and it shows up as an AAC file in both yours and friend’s computers. Is that what you were aiming for?

Otherwise, I’ve heard rumors of people running iTunes libraries completely using SMB sharepoints so they can access the same library on multiple computers. Just don’t have more than one instance of iTunes access the library at any one time, and that should work too.

http://uncanny-valley.com/content/view/10/27/

Of course, I happen to know the guys who wrote it.

~jeff
co-author of Daappelganger