Need software for syncing iTunes on macs and a server

Not sure if anyone has my specific setup, but suggestions are appreciated.

Hardware:
2 macbook pros
1 windows home server

The goal is to have identical copies of my iTunes music folder on both macbooks and the server where all edits (adding/deleting music, changing tags, etc) are made to one macbook and flow through to the other macbook and server automatically.

I have shared the libraries on the macbooks, but when viewing another computer's library in iTunes, it doesn't give the nice UI and these laptops typically aren't on the same network so I'd like a copy on each.
The server needs its own copy for a connected HTPC which runs WMC. I manually add a "folder.jpg" to the music album folders for the sake of getting album art on WMC. So I'm looking to sync all files/folders rather than something that will scan for mp3s and wind up leaving out the jpgs in all the music folders.