I think my way of listening to music is a bit similar to this. Basically, I use ncmpcpp's "Add random songs" feature with an arbitrary number (let's say 50) to fill up my queue with some stuff from my library. Then if I decide I want to listen to something particular, I search for it in ncmpcpp and then just add it at the top of my queue. It plays it next and then it continues with my random items. My queue is always on consume, so all of the items disappear from the queue after being played/skipped.

Of course, the main "issue" with this is that after the end of the queue is reached, the playback stops. I don't actually mind this, because I can schedule my playback to stop by moving my current item + how many else to the end of the queue. I know that there's a deamon to automatically add random songs at the end of your queue once you run out of stuff in case that's a hurdle (https://github.com/joshkunz/ashuffle).