Because, when they did it right, in Windows NT 3.51, the users with legacy 16 bit applications screamed. There was a 16-bit DOS compatibility box, but it wasn't bug-compatible with DOS.
Microsoft underestimated the inertia of the applications market. NT 3.51 was fine if you used it as a pure 32-bit operating system. You could even configure it without DOS compatibility. Few did.
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