I don't see Windows as having much of an edge there. Lots of things seem to change on Windows just for change's sake. I get so tired of the churn on Windows versions and finding how to disable the new crummy features. If you want to avoid relearning all the time, something simple like XFCE is going to be way better.
I feel the need to constantly reiterate this; if someone who works on Windows Update reads this, please consider a different career, because you are categorically terrible at your job. There are plenty of jobs out there that don't involve software engineering.
To the average user, it absolutely will. Unless they happen to run on particularly well-supported hardware, the days of console tinkering aren't gone, even on major distros.
What's fixable to the average Linux user and what's fixable to the average person (whose job is not to run Linux) are two very, very different things.
I would expect that booting from an older kernel would work, possibly in recovery mode.
Windows system restore has never worked for me.
The biggest brick event in recent times was Shockwave, not Windows. Personally I've never seen a bricked machine, not at home, not at work, not at family.
Of course my anecdata is meaningless as is your annecdata. Ymmv.
This is the second time this has happened to my family from Windows, on different computers.
But they specifically said it is not about OS, but about programs on this OS. There is Windows-based software that looks the same as 2 decades ago.