I think the difference is in the second step. Both companies excel in moving the target forward, but Microsoft rarely, if ever, shuts off access to the old targets, maintaining compatibility essentially forever, which keeps them from ever being able to make major transitions.

There are any number of ways to develop for Windows, and the fact that many, even most developers use Visual Studio is different from the Apple approach: everybody must use Xcode. This sucks for companies like MetroWerks that once developed a popular IDE for MacOS only to be shut out, but it's necessary to ensure that the tail end of the migration, that pesky step 2 of shutting things off, happens.