I’d rather break things in favor of something better, and provide a way to make the old thing run, than be stuck with ancient baggage

Windows is office software first and foremost, designed to be used by people who neither know nor care what an “operating system” is. Every last one of these people is entirely incapacitated by even the most lovingly-crafted and descriptive error message. If Microsoft ever considered a policy like this, the city of Redmond would be razed to the ground inside twelve hours