If you're a company the size of Microsoft, "hard" just means "expensive." There is certianly no question that Microsoft is able to produce Windows updates that do not have these problems. Apple has been doing automatic updates for years - but we don't hear similar stories coming from that camp, because they put in the necessary QA effort.
I can imagine there was tense meeting somewhere in MS where the choice was made to stop the update. I would have liked to have been there...