It feels like a lot of Microsoft software has a very "eh, fuck it, whatever" kind of attitude, especially when it comes to troubleshooting. Lots of good intentions that just never get finished.
Case in point, the "Do you want Windows to search for a solution?" Since the day this feature was added I've never once had Windows figure anything out; I always get "Windows was unable…". In the Win2K/XP days, you could right-click on a network adapter and choose 'repair' to do all the standard stuff (flush DNS, release/renew DHCP lease, etc.) which would solve most problems. They took that out in Vista in favour of the "idk man" wizard, and now you have to do it by hand.
Windows is also full of catch-all error messages, where it says "We couldn't copy the file. Check file permissions, make sure there's free space, and if it's a network drive make sure you're still on the network", as if those weren't things that the computer couldn't check for me in milliseconds.
When people say that macOS is falling behind Windows, it seems to be, at best, a superficial judgement from people who don't use both of them for productive work. Windows 10 has a lot of polish, but it also has two separate control panels for changing settings, apps which don't seem to know what kind of apps they are, and more and more new APIs and features that only store apps can use, in exchange for extremely limited access to the system.
Windows is great for playing games, but for any serious work the overhead of making it work and keeping it working is just ridiculous.
> Windows 10 has a lot of polish, but it also has two separate control panels for changing settings...
I've seen this with every new version of Windows (except Windows 8.x, which I haven't used and instead jumped from Windows 7 to Windows 10). With each new introduction and addition of polish, you still see old dialogs and methods of doing things underneath once you go one or two levels in. Control Panel is the best example of this. Windows 10 isn't even a complete OS yet. As an example, if I go to Settings and search for "proxy", nothing would show up. If I drill down into Network manually, then I can see and change the proxy settings. I'm sure there are many other unfinished things in it. It's as if they released an in-progress OS right in the middle of a development cycle, and I find it both frustrating to use and ridiculous!