I had this experience a few years back and just put it in the sorta janky but hacky fun box.
However I did a totally fresh reinstall on some new hardware 6 months ago and it's been absolutely rock solid since and updates have been one click without issue.
Was still a bit of a faff to set up (though tbf that was more around the VM side of things which was my perogative)
I had the exact same experience. I might even have some comments on an old HN account complaining about HA's disregard for upgrade stability. After another broken upgrade, I finally decided to just fix my install at a certain update in March 2022 and leave it there. I left it there for over a year, until I wanted a few newer features. I carved out a chunk of my weekend to make sure I had time to fix whatever broke with everything and... nothing broke after catching up on a full year of updates. It's now faster, just as reliable, and has more features than before.
Home Assistant is finally ready for primetime in the average technical user's home.
I upgrade it automatically for years and they royally fucked the upgrade only once (I had to spend an hour to bring it back to life). Otherwise I never had an issue with my set of devices.
However I did a totally fresh reinstall on some new hardware 6 months ago and it's been absolutely rock solid since and updates have been one click without issue.
Was still a bit of a faff to set up (though tbf that was more around the VM side of things which was my perogative)