3.11 to 95 was a big shift in terms of how the interface worked, but after that it was pretty damned consistent until 8 tried to turn everything into a tablet.

The introduction of WDDM along with the new sound and networking driver architectures caused some headache in Vista, but were ultimately significant improvements over the way things had been.

10, on the other hand, made automatic updates mandatory, and pushed itself on everybody through dark patterns. It puts ads in the start menu and on the lock screen. It started, but didn't finish, implementing new interfaces nobody asked for while deprecating the old ones they still hand't entirely replicated. Today, they're doing their damnedest to hide the fact that you don't need a Microsoft account to set up your computer.