What about PLEX?
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Self-hosted subsonic is not perfect but meets all your requirements.
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Airsonic with Ultrasonic on Android works wonders for me.
End of conversation
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Airsonic with the Subsonic app
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It's theoretically possible to do this on Spotify, but the UX is a bit janky — have to upload from a desktop machine, make a playlist from the desktop machine, then pin it for download on each mobile device:https://support.spotify.com/us/article/listen-to-local-files/ …
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I like iTunes Match though it does have enraging sync problems sometimes
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Plex seems to meet these requirements
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