I felt the same in reverse trying to make a game (Creatures 3) work well on Windows 95/98 in late 1999. We did quite a few patches after release to fix odd compatibility bugs that came in via customer support.

Some weren't directly Microsoft's fault. I remember there was a printer driver that would change the current directory of processes that it wasn't even being used in. I had to update the media code in the game to use absolute paths.

It often felt like I was being paid by my company to work for Microsoft, which felt very clever of Microsoft at the time!

Windows works because everyone, at Microsoft and outside, put in a lot of work to make it work.