plasticcheese,

I was in your position a few years back. I missed MediaMonkey when shifting to Linux.

I found Tauon media player was a pretty solid replacement for playing local and network files, but ultimately settled on running Navidrome server and Feishin as a desktop client. I haven’t looked back.

For organising your collection, I’d look at using either Musicbrainz Picard (GUI based) or Beets (CLI, and it’s a little complicated at first). I generally use Beets with Musicbrainz database, and the Discog plugin for anything not found by MB.

I haven’t found anything that is a complete package like MediaMonkey, but with a bit of effort and once the parts are set up, it’s so much better.

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