I had to get a new headset for Flossie. They do wear down and start to make the bars feel spring loaded. Maybe that's what he was doing with your head tube and bars? Checking for a worn headset?
Flossie also needs a new bottom bracket (crank arms can be wiggled in directions they're really not supposed to go) but since I don't ride Flossie much, the shop said that would wait another year.
You, on the other hand, are a wildwoman on that bike! I'm not at all surprised you've started wearing out parts!