Methods aside, I think it is fairly understandable where Microsoft is coming from. People are conservative and lazy and would stay on outdated OSes for who knows how long, which would force commercial software vendors and in turn Microsoft to continue support those platforms. Which is frankly a waste of resources. Web developers had it with their IE zoo not so long ago, so no thanks =).
It turns out that Microsoft's support is not valued by "lazy people". It might be useful when something breaks, but if it's not broken, why to fix it? Yes, people are lazy and nobody is going to change that. It should be noted here that laziness is actually a form of resistance against the update terror. MS is forcing us to move ot their newest OS and we lose a lot of time just on learning where the f***g buttons and menus have gone to. All this time could be spend on some creative activity, but we spend it reinventing the wheel. A big loss for us, but MS saves some $ on support. Can't they update their business model instead? I'd pay just for not having to change OS.
IE is a different thing. Microsoft has always been setting their own rules rather than following open standards. The strategy has been paying well until the internet boom with other browsers entering the scene. People hated updates in Firefox just as much as they hate them in IE (Windows), but Firefox has been striving to follow open standards from the beginning, so that the developers at Mozilla didn't really need to force people to update, while MS finally got their asses kicked for ignoring open standards.
On desktop everything go out of date pretty quickly and sooner or later you are forced to update because new versions of some essential application is not built for your release anymore. Then you can try to continue to maintain some things by hand but this is a huge step down in user experience.
Joel Spolsky refers to this as to "fire and motion" tactics. The new software is not better than the old one and you don't need it, but you are forced to update so that you don't have time to compete with the software vendor. In the Linux world things seem to be a bit different. In that world it is perfectly normal if someone wants to use archaic software like Vim or Emacs. There are downsides, sure. I go crazy every time when such a basic thing as copying to clipboard doesn't work again
, but that's still better than having to update everything just because some asshole in a suit has decided that you have to udpate.