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.

Not sure why this was downvoted. This has been my experience. It’s quite high maintenance.

"frequently"?

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.

I've had that experience a few times a few years ago, but these days I don't even enable the "make a backup" checkbox when I upgrade HA.

Things seem to break more if you pull in external software repositories (HACS) but that's to be expected.