I'm in experimental mode on this one as well.
Right now, I'm trying to sync the "iTunes Music" folder with ChronoSync. The problem is though that the library information (the actual iTunes database) needs to be updated everytime by doing the command "Add to Library" and then picking the "iTunes Music" folder. That's necessary to let iTunes know that new music might have been added, as iTunes doesn't scan the music folder by itself.
It's far from perfect, so I'm open to better suggestions.
-t