When choosing this path, Microsoft got arrogant and thought they are too big to fail. The IT industry doesn't forgive though, last 30 years have plenty of examples like this. Microsoft need major shake and reality check.
At home I kicked last Windows OS out of the door few years ago.
At work, not so lucky, I still need to support this piece of s***. Every, literally every, Windows and Office update is messing something up. When we see the update window popping up we know it's a sign to fasten the seatbelts and wait for the incidents to start pouring in.