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Selfhosted
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Outside of Plexamp, I'm not sure of any self hosted music solutions that can generate random & context-aware playlists, most of the ones I'm aware of (Navidrome and the various apps that support it) appear to be mostly classic media players as you mentioned. There's also Funkwhale, but that's more of a self hosted, federated SoundCloud alternative I think.
Music discoverability is something I kind of stuggle with when looking to expand my library, so I tend to rely on apps to do this. I personally use Newpipe, as it works for YouTube, SoundCloud and Bandcamp, allowing me to jump between the platforms looking for remixes and the like.
For a more spotify-like discovery experience, the Spotube app combines Spotify's API with YouTube Music to play spotify-suggested playlists, and there's another app SimpMusic that does the same for YouTube music
It's also primarily for self-publishing. When sharing music that's not your own I suspect you quickly run into the same issues as with torrents. With probably similar solutions.
I'll check out Spotube and SimpMusic, although the local music part is missing from your description.