I think I’m going to set this device aside and get a new one. I suspect I might be struggling with damaged hardware. I was able to get through the steps of setting up an ESP32 pretty easily.
Replaced the device and I’ve had no problems. I think I ruined the previous device by supplying 5v instead of 3.3v via the header pins / serial port.
Leaving this note in case someone else experiences this kind-of-maybe-broken state.
If an esp node is working then there’s a really good argument to be made that you can and should in some cases just skip the updates. Looking at this latest change log, I can see that this update has absolutely nothing to do with most of my esp nodes and there’s no reason for me to apply a useless update and especially if it breaks any nodes, I’m sure as hell not going to lose any sleep trying to troubleshoot it. This isn’t Microsoft Windows here and these updates are closing important security issues. It will be OK skipping any that don’t apply to you.