The hollow threat
In all my experience with Microsoft from DOS 2.0 on up, I've never seen anything but the most newsworthy problems addressed. There are always dozens of issues with the OS after an update, and in many cases many more, having been added to by the supposed update itself. The continual threat of loss of support is a red herring. Unaddressed, legacy vulnerabilities and bugs continue to exist even in the most recent Windows iterations. So what, exactly, does one lose when so-called 'support' is dropped, aside from the joy of trying to get previously stable programs to run on the new release?