I would say that the main difference is that many applications written for Windows 95 will work just fine on a Windows 10 system. The Mac ecosystem has nowhere near the same amount of longevity.
With some tweaks, Deus Ex Invisible War runs fine here on Windows 10. In general i didn't had any game or program i couldn't get it to run in Windows 10 and i have a lot of older software.
Microsoft may shit out a new toolkit every other year (which is a shame, they should be fixing their existing stuff instead) but at least they maintain them for basically eternity. You can pick up anything and it'll be there for years to come (though not everything may be bundled with the OS forever - IIRC some less used some are downloaded on demand, but still the applications do not break).
(though personally i mainly trust core Win32 as everything else is built on it and because of that it is the most likely to remain stable)
If FillRect(hdc,rect) is the only thing that you need from it then it will work for you, yes.
But GDI does not support antialiasing so, let's say, Ellipse(hdc) will just draw an illustration to Brezenham algorithm but not that you would want to present to the user.
Same thing about alpha channel - no transparency in GDI.
So forget GDI for UI purposes. You may try to use that GDI+ horse... But it is pure CPU rasterizer and so forget it too on modern high-DPI monitors.
Yes, GDI is still with us but the chorus is here already to sing "Sic transit gloria mundi".
I use office because that's their biggest money making client application suite. You would think it gets the most UI usability focus of any of their products, so it must mean something when they don't use any of the UI frameworks they push for everbody else.
Visual Studio is an interesting one, huge effort to get working on WPF, which needed improvements to WPF for them to use it. Surprise dog fooding your UI framework causes improvements pretty quick.
Imagine what WPF would be like if the Office team used it, might be cross platform.
Luckily for GUI apps I've had enough "wisdom" and am only using Win32. Delphi (another shining example of backwards compatibility and being TRUE RAD) has shielded me from writing too much code for functional GUIs.
So I mostly work on improving functionality and feature set rather than chasing whatever latest tech/framework is in vogue at the moment. Most of them come and go. Especially in web development.