Maybe the jeep is a "guy" thing that will serve a couple of purposes. First, H is excited about it and that is a good thing, and secondly, so is son. So the jeep may provide a lot of valuable bonding time between the two guys in your life. (I know we've had a 67 Mustang for about 25 years now, and it is the one common bond between H and S14).
I do hope the ow is looking for other employment. With her out of the office, I think many of your insecurities will disappear and some of the stress on H will loosen up a bit.