A few challenges popped up, the first was playback sync. DLNA is great, but it can't sync playback across speaker endpoints. So I plan to use MediaMonkey on a Mac so it can use the built-in AirPlay+Airfoil servers to (selectively) play audio in sync.
The second challenge was getting MediaMonkey to a Mac. After Wine kept failing (it would launch but show no GUI, crash constantly, freeze drawing a giant block of solid color on-screen) I switched the approach to Microsoft's RDS RemoteApps. It showed the same glitches/crashes as on Wine, but I found out that as long as I didn't mess with MediaMonkey's window (minimize, resize, open Settings/Preferences) it stays reasonably stable--that's fine since it's a headless Mac anyway.
The last challenge was actually what I thought would be the easiest: controlling it remotely. Other than remoting into the Mac and risking crashing it, I, for some reason thought would be able to control it from another MediaMonkey instance. I have an automation server that behaves like this, it pulls licensing, devices, logs, etc as if it the server logic was running on the remote clients (iTunes Remote does this too), maybe I got that from this, but I'm hopeful: can this be done in MediaMonkey?
I still have another, maybe two options more, fortunately, but since MediaMonkey is the paid of the two (or three---fingers crossed) I thought this would be all sorted out. Maybe I just haven't found the appropriate settings, there are a ton of them--which seems like a good sign.

Is this possible? (if so, how?)
Thanks in adv.