With the steel 27 x 1 1/4" non-hooked rims from circa 1980s Schwinn and French wheels from a Peugeot UO8, I've been able to run Bontrager Hardcase rims. I haven't tried a Gatorskin.

I don't think I've inflated them to more than about 85 psi though. I fill them to 100-110 but I lose alot when I pull the filler nozzle off. I'm going to get Presta valves in the future to alleviate that.

The bike and me weigh about 340-350 lbs total when I have stuff in the panniers. (I'm 295 clothed.)

I would blow cheap Kenda tires off the rims like nothing if I filled it to that pressure. I would also flat the Kendas at least once/week so they were awful for me.

The Bontragers were hard to get on the first time, but they loosen up quite a bit with use. I typically flat one of them once every few months.