One either have to rely on everything being updated in lockstep with everything else, or expect to do some massive backporting.
This because outside of a few projects, the kernel being one of them (Qt being another, oddly enough), nobody can be bothered to actually adhere to API, never mind ABI, stability beyond their own use for them.
I would confidently install new updates, secure in the knowledge that if it broke something, I could roll it back. But Microsoft has so little faith in their updates that they know that they have to cram them down our throats.
Of course the narrative now is that everything must be "evergreen", so that they can find new ways to insert ads into our desktops, and deprecate features we depend on.
Just off the top of my head, I've seen so many "home users" get burned.
My grandmother's copy of Skype on her PPC OSX Leopard stopped working, so I had to nullroute ui.skype.com, and revert the update with Time Machine, and it started working again. When they said it was a "critical" update, they were lying. It worked just fine when I reverted it and disabled the updater. The update was purely there to deny service, and remove all functionality.
Or my grandfather's Kindle updated itself to disable encryption. Don't even get me started on the "helpful" updates for the Kindle. My grandparents recognized it for the scam it is.
And I'm pretty sure that "transparently" installing updates is not for convenience, it's because if you explicitly told users what you were doing, a lot of them would want to say no. If you simply had a dialog box detailing exactly what the update had just done, people would not be happy. So instead, your software landscape is just one where stuff shifts around and disappears at night, and you have to pray that the next update won't break something.
That said, it is hard to find a good time to do updates, and not everyone notice that popup about "we are about to reboot for an update" while in the proverbial zone.
Also, they are highly deceptive in how they push them on us.
Finally, my computer is important to me, and I can't afford to be their beta tester. My computer isn't a toy.
People hold up on doing updates because they do not know what will break, and they need the computer to work 24/7 these days to stay in contact not just with work but also with family and friends.
And it is not only the major updates.
I have a laptop here, built around AMD parts.
when AMD introduced their Crimson driver set, they also discontinued support for the APU part of this laptop.
But still MS tries to be helpful and push out updated driver files, completely ignorant of the issue.
Thus at random intervals i can expect my external monitor to stop working until i go into the device manager and roll back the driver for the APU.
Edit: bah, scratch the part about "and me" up there. Thinking back i had to grab some tool at one point and actually blacklist a patch from MS because it would attempt to install, reboot, fail to come up a few times, then roll back, reboot, come back up, and then try to install again a day or two later.