It's situational, I'll tell you that. I build PCs and repair them as a side hassle and I'm not saying I never come across issues with Windows (even dating back to the XP days) but I find the troubleshoot process much easier than on Linux regardless of the distro. What I mostly come across is viruses and malwares which I have to clean up on those machines.

Windows breaks in all sorts of new and interesting ways when it finally meets the real world.

I would love if you could elaborate on that, I don't want to misunderstand. If I have to guess, for some users the "real world" doesn't go past office work.

I don't doubt a serious Linux power user would find their way out of most situations. The steep learning curve for Linux is what's keeping most people (the ones who don't need rely on Windows for some types of exclusive softwares) from switching. When I first "switched" I was a 16 year old with a lot of time to spare and I started figuring it out to an extent. Can't say the same about everyone, at least not the people that come to me asking me how to stop programs from opening on their own at startup.