So I've been wanting to figure out a way to sync two folders, both ways, so basically files can be added on either machine and end up in both places. There's an app called ChronoSync that does exactly what I'm looking for. I was going to tinker around with rsync but this seems like a much easier solution.
Basically the problem I am running into is I have two desktop Macs and a file server and I tend to have files floating around on each machine. For iTunes I am also using Syncopation to sync the iTunes libraries. The added advantage of this is I will also have 3 independent backups of my music. So if I need to take down my file server for whatever reason there should be no interruptions. iTunes is flakey with libraries on network shares anyway. If you happen to not have the share connected it will sometimes flag your entire library with a ! which, as far as I know, is basically fatal. When that happens I have to re-create my entire library.
Once I'm sure this actually works I'll probably write-up some details. I think I'm not the only person running into this problem. It takes 2 or 3 different apps to get everything glued together but it's pretty easy to setup.