I like Media Monkey, too. Perhaps you can find some kind of library/streaming software for OSX that ISN'T iTunes. Dunno. Not my thing.

Last time I looked at FreeNAS, it would not run SqueezeServer (or wahtever the server side of Squeezebox is called now).

It would be hard for me to have to choose between going to Windoze where none currently exists, and learning to tolerate iTunes. Good luck with that.

bibere usque ad hilaritatem