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.
macOS is also quite a capable workstation OS that needs no account other than a local account.
Windows 10 Home you cannot even create a local account without having the Internet disconnected.
Pretty sure the same stands for Android.
Sure I would say this would make it more of a feature phone but the device itself is quite usable without an iCloud account.
One reason for this, interestingly, is that NT had less of a past to deal with - it was a clean-sheet design by one of the most experienced OS kernel designers on the planet (David Cutler, from DEC) - Linux was still trying to be "Unix-like" and maintain (more or less) POSIX compatibility (though to be fair, POSIX didn't show up until about the time Linux grew out of its hobbyist toy phase...)
In the simple sense that you can run ancient Win 95 applications in any of these later versions (if not 3.11 and DOS too).
In theory, according to MS. In reality we all have seen old applications die when windows updates. Security-related applications are notorious for this. What once worked perfectly well with Win8 now goes into total panic mode when it sees Win10 doing its thing in unexpected ways.
I wouldn't expect "security related" applications to work (e.g. some antivirus), as they use bizarro / too low level APIs.
But you can still run 15+ year old games, office apps, and whatever...
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.