@darius i am in a weirdly similar situation.

i am using plex until i find something more suited for me. i don’t love it but it has lots of itunesy features and i can use first-party and third-party clients and stream music from home when i am out with my phone.

i am using beets to organize/tag my files, and the plex server just mindlessly reads from that library.

my most used plex feature is the plexamp client’s “random album radio” which just plays me random albums in order!