I just don't update home assistant monthly. Maybe once or twice a year? Tbh that seems to work super well. Never have to think about it and it just works.
I take a similar approach to firmware upgrades for my IoT devices - I run them on a couple of separate vlans, so I feel okay only updating them every few months when I see the need (mostly custom builds of tasmota/esphome/etc.)
HA is not ready for grandma, but most technically inclined folks should be able to get a ton out of it after you get past the initial learning curve.
The add-on actually download the new version and checks my config file against it. When something breaks, you get the error message so you can fix what's not working (happens once or twice a year for me, usually a config change), and relaunch the add-on to test again.