So I've manually swapped about 6 or 8 tires total since I started this thread.
I made a bead breaker to make it easier - just a 2x8 with some fancy woodwork on the end that I use as a ramp. (Note: support the ramp in the middle or you'll crack the 2x8. Ask me how I know!)
Another important thing I learned: temperature is important. I tried and failed to get a tire off a rim about a week ago when it was ~14 C outside (57 F). Couldn't do it. Then I brought the wheel inside beside the fireplace, let it warm up, and it went MUCH easier.
I Also learned that tire construction makes a difference: the 165/65R14 RE92's you can almost install on a rim entirely by hand (and feet). But a RE92 in 175/64R14 size was noticeably harder to do.