Windows has always been two creatures that behave in very different ways. The server line is where you see stability and compatibility reign supreme.
On the desktop/workstation line though, let's take a trip down memory lane and remember all these upgrades together: Windows 3.11 -> 95 -> 98 -> Me -> XP -> Vista -> 7 -> 8 -> 10.
I am having a really hard time seeing how one can infer from that timeline that Microsoft's desktop OS line follows a philosophy of "catering to the user, keeping things consistent, and being backwards compatible." Windows 98 didn't cause much hassle, but, at least from my experience, that was really it. Windows 7 had its share of hassles, too. Particularly, as I recall, in the backwards compatibility department. We just remember it fondly because it was sandwiched in between Windows Vista and Windows 8.