finamp is missing enough features to me to make plexamp worth paying for to me (not automatically switching to transcoding on mobile data, not supporting opus transcodes)
I don’t use MacOS, but it seems like you can disable Gatekeeper with the command line. I doubt a change in its behavior would make a difference if it’s disabled in the first place.
vagina bones is a meme from a guy on 4chan complaining that nintendo censored a character’s “vagina bones” in the western release of a game. this meme isn’t serious
plex/jellyfin server with wireguard running on your router would probably be a good setup as long as whatever device they’re using supports wireguard