So I was fine for another two years on Ubuntu until another dist-upgrade broke everything again. Sensing a pattern, I decided to give Pop a try.
I'm now about a year into Pop and sure enough, a few weeks ago a dist-upgrade broke a lot of things, but unlike Ubuntu, I was able to find System76's tech support page, I ran the commands it suggested, and everything's fine again!
https://support.system76.com/articles/package-manager-ubuntu...
Miraculous, I tell you.
I still can't figure out why there are multiple versions of some things in the Pop Shop, but they all seem to work, so I'm not complaining, it's just weird. Someday I'll figure out this whole tiling-windows thing, but I think that's for people with bigger screens so I turned it off so my alt-tab reflexes work again.
In general, it just works, and that's more than I can say for Windows or Ubuntu at this point.