That was then. Recently my wife wanted a durable portable speaker, and got a JBL somethingorother. It works surprisingly well. So I got some JBL earbuds. They work pretty well. I got curious and went back over some old headphones. Turns out some of the problems seem to be in the stack and some in the devices - I ended up not using those old headphones, but some of the old problems did get fixed.
In summary: Things used to suck but my recent BT purchases have set me hopeful. I use the auxiliary port on my car still also - and I think I'll keep it that way for sharing. Pairing devices still makes me feel invaded.