The next test will Be Win7. After that, maybe, Win 8.2 on UEFI. But that would mean risking a micro-pc, with a notebook drive, that I don't have a replacement for. (Without a 2nd 2.5" notebook drive for the test, I'd be running a risk.)
I have Emby installed and running in DOCKER but it's not working or, more accurately, it's doing something "weird". I successfully attached Emby to a music share. When I play a song, the controls bar comes up and immediately drops, without a sound. After playing with it a bit, I did the "auto mix". What I saw then was the player cycling through song titles at the rate of 1 or 2 a second, as if it was playing them really fast. Again, not a sound. I downloaded Emby theater (as if a client would be better than a Web window). The behavior was the same. Have you seen this before?
My Emby usage is through Kodi on a Pi 2B there is a Kodi sync plugin for Emby, that way it works perfectly as it uses the Kodi player + I can control Kodi from the iPhone app.
I can also get music to play and shuffle using vlc and just point to the Music samba share, it also works on our PS3 using dlna, this uses the PS3 player and it shuffles tracks with the info being displayed on the TV.
TBH I've never used any of the 'addons' i.e. theatre etc as there are other ways of streaming, I've used Emby as a backend for Kodi. I did try Docker, but when I moved to v3 I used the apt tool which works perfectly, even the updates come through.
Raid is not a backup! Would you go skydiving without a parachute?