I got around this by developing smart playlists which rotate in stuff I like based on tags and then filtered by how recently the songs were heard or skipped.

However, this requires a truly autistic dedication to not only maintaining a local music collection, but tagging the shit out of it, and developing complex queries (in Quod Libet) to make smart playlists for all manner of different moods & hankerings.

If you are a computer-touchy autist with a local music collection though, Quod Libet might just be the tool for you. I do abuse playlists as tags because the UX is better in a lot of ways.