Yeah, I have to use Microsoft products for work and I’ve stumbled across their forums for issues before. I don’t think it’s ever once been helpful. Solutions on Linux forums are hit and miss, but still much better.
I use mpd-sima for autoplay functionality. It would in turn require using mpd or mopidy.
It queries last.fm for recommended artists and tries to find a match in your playlist. It works, but honestly it’s not great. I don’t think it’s any fault of the software. Last.FM doesn’t know your library and seems to return limited results, so it’s like a game of battleship actually getting a hit. (Not quite that bad, but the analogy holds water, overall)