This may sound unexpected, but the Win32 API is still perfectly functional, and is probably your most solid foundation for any native development efforts you want to ensure continue to work long term. It's found a degree of support on other platforms (e.g. Wine/Proton, even quirky upstarts like ReactOS) and if Windows goes the way of the dodo my gut says the industry will find a way to breathe life support to that layer. As a bonus your binaries can be small and self-contained. .NET looks like its future is bright as well (was really glad to see Core, open sourcing, and their strides to unleash the stack beyond Windows).

No inside info here, but as a lifelong Windows developer and user, I'm disappointed in the route Microsoft took with their OS. Feels like decades of poor business decisions and squandered opportunity. Throwing all kinds of new methodologies out there without a clear vision. Arbitrarily designating older technologies as outdated then doing a poor job of reinventing them (looking at you WinFS), and an obsession with trying to add "more" when cleaning up and refining what they had first would have served better. I'm still annoyed by the whole "we need to fatten all our directory names to show off long filename support" which to this day left us ugly artifacts like "Program Files (x86)", linked folders you can't easily open, redundant places for registry settings (...don't forget SysWOW64), autoruns spattered all over the place (the SysInternals tool of the same name does a great job of surfacing), the list goes on. The transition from 16-bit to 32-bit was cleaner than 32-bit to 64-bit, I suspect because the developers who worked on the former were "closer to the metal" and could just make the changes in the code instead of spending 10X the effort on workarounds. If there are insiders in the room who say otherwise I'd love to be corrected.

Windows 7 was the last edition I could tolerate. The user-hostility of Win 10 and 11 is a non-starter for me (ads, telemetry, ramming broken updates down your throat that brick your PC as the worst time, their trajectory toward forcing TPM so that you no longer own the keys to your castle, etc). They're copy-catting some of the worst practices by competitors in a big race to the bottom. It's a real shame, because the kernel team made some great improvements under the hood in the meantime.

If this sounds like an old person rant, I guess it's because it is. It hurts, as I grew up with this OS, became incredibly proficient with it, gathered and built an ecosystem of tools to support how I work, started a business on their stack, helped customers adopt it to be successful, cultivated a reputation, etc. I still hope someone with authority at Microsoft smartens up and sets a course correction, the way they were late but eventually did embrace the Web and open source. I was always skeptical of the whole "Windows 10 is the last version that will ever be" nonsense, and waited it out hoping when they readopted version numbers Windows 11 would arrive along with a renewed focus on putting the user first. But at the moment I'm resigned to the likelihood I'll have to figure out which version of Linux will work best for me and get serious about adopting it.