So I'm all for solving current problems, however if I'm sure of anything, I'm sure that companies like Microsoft or Apple won't deliver a solution that solves these problems without locking-in users into a trap which is worse than the problem that it's solving.
And on Windows, this is the oldest trick in the book - in order to sell something people don't want, you first need to create the demand for it.
Because the fact remains - computers have been a difficult thing for many people to use and maintain reliably. The "Windows has been historically shitty" point might be a reason this problem has been worse than it needed to, but it's hardly a compelling excuse.
When people—and not just Grandma—point out that their iPads don't have the same problem, then we should take that on board, rather than telling them that they're stupid for not listening.