Indeed. Let's explore that a bit...I don't disagree with your overall point either. But I think there is room for both "types" of computer user to exist: those who wish to learn more and explore further, and the "tablet generation" who just want the damn thing to work.
The "tablet generation" are increasingly moving to, well, tablets and such. Their world is increasingly WEB based. Gmail, FaceBook, Google Docs whatever. No worries about operating systems, installing applications, device drivers and so on. As long as they have a browser they are in business.
Currently the "tablet generation" are a bit stuck on "apps" and app stores. Android apps iOS apps. But they are almost indistinguishable from WEB apps, you search for what you want, hit the button it downloads and runs, no hassle. Soon HTML5 and future web technologies will enable all of that to happen in the browser at which point it no longer matters if you are on Android, iOS, a Mac, a Windows box.
For the "tablet generation" Windows is becoming totally irrelevant. As are all operating systems under the browser. Only performance and price is an issue.
Ultimately MS cannot survive here with Windows as they need their users to pay for it and users can run their browser by other means.
Those who wish to learn more: Well they are going to find that their progress is blocked in all directions by the closed source, proprietary, expensive, inflexible, operating systems of yore. The Pi is part of that movement away from the old ways.
MS cannot survive here with Windows either. Eventually the human population outside MS will code up everything they want, the few thousands of developers
inside MS cannot keep ahead of that forever or even much longer.
In general I see Windows and MS apps as a solution to problems we don't have any more. Word processing for example took off like crazy with the advent of the laser printer. Hence WISIWIG. No one want's to print stuff any more. If they write anything it's on forums and blogs and their own web sites. MS Word is like selling buggy whips to the generation that started driving cars. PowerPoint is looking increasingly stupid when you can make most of what is in normal presentations on web pages and have them available to anyone from anywhere with ease.
What's left in this picture? Ah yes, the power users. Those who need their CAD package or whatever which does not fit on the web paradigm yet, to big to slow, whatever. In the ever shrinking Windows world the cost of maintaining those packages there will become prohibitive, they will get ported to other platforms.
Do you actually want to be an SQL Server and .NET/VB6 developer? I believe there is therapy for that:)Personally I'll never be able to truly get away from Windows, at least not as long as I want to continue being employed as a SQL Server & .NET/VB6
As for that ZIP in Windows thing. How come on my friends XP box where I have sometimes needed to unzip files always pops up winrar or whatever it is called nagging that I should register and pay for it?
And another thing...The last, perhaps only, useful program that came with an out of the box Windows install was HyperTerminal. It was a crappy terminal program but it did at least let you talk down a serial line. That is no longer bundled with Windows. There is nothing left at all any more.