Try out the AirPods, all three of your issues are addressed. Sound quality still doesn't remotely rival my studio monitors, but I also wouldn't be caught walking down the street with them either. YMMV!
I wrote them off immediately because they look identical to the pack-in iphone earbuds, and those are unbearably painful for me to wear.
Guess you don't have an Apple Store nearby?
That said, if the regular Apple EarPods were as painful as you describe, then you'll hate the AirPods. They are almost identical fit wise.
They look very similar, but something about how their weighted changes the fit.