Because its UI and user experience are a shitshow. Settings are scattered everywhere. Windows have no toolbars, title bars, or borders to distinguish them from the one they're overlapping. Menu bars are missing. There are access-prohibited shadows of user directories all over the place in Explorer. The color-scheme editor is simply gone. It's still full of peek-a-boo and Easter-egg UI, with controls disguised as text or simply invisible unless you accidentally roll over them.
And my favorite: Microsoft has disabled remote desktop access except in its "pro" version. Gee, Microsoft: Your contention is that a PROFESSIONAL is the most likely customer to need someone else to log in and help him remotely? Retarded.
When my parents have an issue that I could log in and solve, guess what? I can't. And no, Microsoft, I'm not "upgrading" them to a "pro" version of your broken shit. I'm going to buy them a Mac, and that's the end of Windows in any of my family's homes. And this is coming from a former Windows enthusiast / professional developer / Mac scorner.
You don't realize how unusable Windows has become until you try to set someone up on it. Its E-mail program is absymal, defective in design and function. Outlook isn't included anymore. If you do make the mistake of installing another glorified spam conduit, Office 365, you'll be treated to defects that literally render it unusable to some people: I increased the system-wide font size for my parents, but Outlook didn't honor it. E-mail subjects in the In box remained microscopic and illegible.
And of course there's the endless goddamned harangue to log in with your Microsoft account. A huge portion of the population is laden with an ever-growing pile of accounts and passwords. An account to log into your computer. Another for E-mail. Another for Apple products. Another for your cable provider. ENOUGH. They have no idea which one I'm asking for when I need to get their password to help them with something.
It's easy for the Hacker News demographic to forget that PEOPLE DO NOT UNDERSTAND THIS MESS. And so they are writing down their IDs and passwords on Post-Its and putting them on their computers. They are using the same password on every site that demands that they use an E-mail address as a user ID, because they think that this is required.
Then the users feel dumb and blame themselves for problems, which pisses me off even more. They're being TAKEN ADVANTAGE OF BY MICROSOFT and others, rendering their computers essentially unusable and their security at risk. It's disgraceful.