I’m not well versed on the Mac side of things but there was a shift in how the updates were handled (at least on Windows) which MIGHT be part of what’s going on.
I don’t even know what “rumps.pyc” does, but I’d suggest moving it to somewhere else and doing a test run rather than deleting it.
My GUESS is that you’re probably going to end up running a manual install over your current installation to get over the change-in-update-process hump.