You may remember that Microsoft wanted to move to an annual subscription model for Windows. I distinctly remember Balmer rubbing his hands together and cackling with glee about how they were going to make much more money that way (as he pushed another couple of nosy kids into the oven of his gingerbread house).
As it turned out, this made an enormous amount of people unhappy. I think they abandoned it.
Apple does have an annual subscription service, MobileMe (or whatever they are calling it this week). As far as I can tell it has had a very low rate of adoption, despite coming free (for a limited time) with new Macs. Heck, I have a hard enough time convincing random (Mac using) strangers to buy a damn external drive and turn on Time Machine. Don't underestimate user inertia.