Windows as iTunes "Master Library"

I'm probably trying to make this more difficult than I really need to...

I currently have 3 computers that run iTunes - Windows Server 2008 r2, Windows 7, and MacBook Pro running Maverics.

I want the Windows Server (it behaves exactly like Windows 7) to be a "Master iTunes Library". Basically, I want this computer to have every song I own. When I want that song on my Mac or Win7 machine, I can copy it by just dragging and dropping it into my library. That's the easy part.

The difficult part is, if I add a song into my Mac or Win7 machine's library, I want it to automatically copy to my server's iTunes library, and stay automatically organized using iTunes organization feature.

Is this possible?

If so, that would make it easy for the Win7 machine, but my MacBook is not always on the same network as my server. Maybe have a script that can kick off the "sync" process?

Any thoughts?