The issue is much simpler, and driven by each and every one of us. We all want to make happy use of Moore's law, we are all far less tolerant of issues caused by IT, we all want more for less. Functionally, DOS 2.1 with Supercalc and Wordstar would be perfect, eh?
That continual drive for faster, better, easier has a price to pay. Microsoft are dominant and therefore have to shoulder responsibility for the systems they sell, but actually they don't make too bad a fist out of it, much as I loathe, hate and despise them, up against Larry Ellison or Apple they are of a piece - possibly on slightly higher ground. But then, they make a change like removing the option to update or not making updates compulsory, and everyone is up in arms.
So anyway, systems will continue to improve and it is not unreasonable for any supplier to charge for new versions (MS is moving to a subscription model) , but that's only the OS side of the story. Over that, there's the middleware and the application, each of which will have their own vulnerabilities and upgrade path.
Right at the sharp end is the application vendor, who effectively integrates and supports the whole thing. Those applications are what you, the end user experiences. Doesn't matter how complex the system is, you just want it to work. And importantly, carry on working. That's where software maintenance comes in. Except that maintenance only covers that version, never the upgrade. And organisations like NHS would be penalised if they tried to salt away money for the next version (even if they could afford it). Simply, in public finance you use it or lose it. Plus, the overwhelming majority of businesses I see, whatever sector, never invest ahead in the "next version", if you are lucky they will cover hardware refresh.
So, why does anyone expect any different outcome?