I think what it really comes down to is that Microsoft is and was ungovernable.
Contrast that with Apple:
Nothing major happens at Apple without direct Steve involvement. Some minor tasks also cannot occur without passing through the Steve prism. You should probably trust me when I say that Apple’s decline in typography can mostly be ascribed to Steve’s not really giving a shit.
Which brought to mind Aaron Swartz’s thoughts on taste:
Negative taste is the ability to tell when something is bad. Positive taste is the ability to make something that is good.