The last few updates I ran on my Windows desktop and Surface Pro 3 have gone without a hitch. When I upgraded my 2013 Mac Pro to High Sierra, the install hung and left me with a partially working system. I had to restore from backup and try again. It worked the second time, but still...
I've been using Windows 10 side by side with macOS for a few years now and while there are still things I prefer about macOS (native UNIX terminal, iTerm2, Messages, Finder), Windows 10 has not been so bad. I prefer macOS's interface (to me, Finder > Explorer), but much of the hate I've seen thrown at Windows 10 either doesn't seem to affect me, or is simply just blind hatred similar to what I've seen Windows users have against macOS in the past.
YMMV I suppose.