Apple Watch not playing music to headphones

I have a series 8 Apple Watch running 10.6 software and an iPhone 13 Pro running 17.5.1. This issue was been going on for a while now. Getting music to play from my Apple Watch (downloaded and stored locally on the watch) through Bluetooth headphones is almost impossible. One of two scenarios will happen when attempting to play music from my watch to Bluetooth headphones:

1) I turn the headphones on, they connect to the watch, I press the playlist to start playing music, I hear it in my headphones, go outside for a run, only to find that the music stops after about 25 yards away because for some dumb reason the music was playing from my iPhone. I typically will then have to go through the steps listed below in scenario 2 (while standing outside wishing I was running); its never as easy as connect headphones to watch, select playlist on watch and press play.

2) The same headphones I always use won’t connect to the watch (when I select to connect it just has the spinning “thinking wheel” which never stops), so I have to forget the device, set the headphones to pairing mode, and try to connect. This works about 50% of the time. Sometimes I have to turn the watch off, power it up, set the headphones to pairing mode, go to Bluetooth setting on the watch, connect, and then they are connected. However it will still usually play the music from my iPhone if its nearby.

I would say that playing music from my Apple Watch to connected Bluetooth headphones works about 20% of the time; probably less.

Is there a fix for this?? Maybe a setting I need to make? If I can’t play a downloaded playlist from the device itself without going through a bunch of asinine steps, then what’s the point in having it?