In a way HA is fundamentally an operating system for your home. It does target more technical users than Joe consumer but not by much in the grand scheme of things, especially as they intend to make it more and more 100% web driven, sell "plug in and go hardware", etc.
The plug in and go hardware is interesting because when you think about it a user who is intimidated to flash an SD card and stick it in a Raspberry Pi is going to have quite the shock when an upgrade eventually becomes necessary and they encounter the challenge that is trying to upgrade even a many months old HA install (forget about years).
As they target more and more users of less technical ability and sophistication this is going to only get worse and worse. If you look through this thread even the HN crowd (which leans heavily technical) is saying things that essentially come down to "the last thing I need in my life is more time spent on Github issues and random forums". Many of them end up going back around to "full home luddite" mode because they just can't stand to have to debug a light switch.
I appreciate this all too well. Many people who know me (their nerdy friend) are surprised I use iPhone, Mac, etc. I simply tell them something like "when I spend all day doing the hard tech stuff I have to do I need to be able to turn that part of my brain off and use something dumb". When I'm checked out and burnt out yes please give me the Fisher-Price experience that is the iPhone.
The issue with your upgrade approach is the same thing as all rolling releases - the more time that goes by, the more likely an upgrade is likely to break things even worse.
If you peruse the HA community forums, reddit, Discord, etc you will often see advice like "if you're not going to upgrade every month when you do upgrade do it progressively through each release", which is still and arduous and very time consuming process.