I think at the end of the day, they are happier with an illegitimate Windows user, than a non-Windows user. They'll nag, push, try everything to annoy, but they won't lock you out completely, because that could mean losing you for good.
Of course, I can only infer this from their past behavior.
Remember all the talk about "Windows as a service"?
Given what's happened so far, I fully expect them to try something like that at some point. "We only offer subscriptions of the latest version, and your current hardware doesn't meet our minimum requirements, so you'll have to replace it to continue using Windows." Maybe it'll trigger a mass exodus to Linux --- or perhaps more likely, back to older and cracked pre-subscription versions of Windows.
A similar scenario is not impossible. Somehow it has become acceptable to use a always-online workflows. There are complete lines of products that won't work at all if you're not online, and some will switch off after a certain time (like Adobe). There is an enormous push in that direction from all industries. People give in without any resistance. It's become normal and acceptable that pieces of code on all your devices connect to different services and send data you have no idea about. If an app stops working because you lose the internet connection, somehow it's not the problem of the app but yours. So I can imagine a scenario similar to the one you describe in a decade or two.
