First off - always try the trial version of the software.

Secondly I have searched far and wide for a solution that would synch multiple mac's iTunes libraries. TuneRanger is that solution. I've tried rsynch and a myriad of other build in unix utils to no avail.

The one quirk that I found is that it is indeed super picky about tagging. You can't go changing tags once everything is synch'd because it will find it as new material.

I was able to get it to work after some tinkering around, intuitiveness is a little off, but over all it ended up being the right solution for what I was trying to do in keeping to macs synch'd with the same stuff in their respective iTunes libraries.