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This is FAR from a click or two but I have wanted to do something similar. I haven't had the time to dig into this yet but I came across https://github.com/teticio/Deej-AI which is a way to train models based on your personal music library (among other sources). Ideally from this you'd be able to create Jellyfin playlists but using the Jellyfin API: https://api.jellyfin.org/#tag/Playlists
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For the multi-room audio, check out snapcast. If you like it, we could try to convince the Symfonium dev to add the ability to cast music directly to snapcast, which I would love to have!
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