"This is Microsoft's vision of what the next generation of computing is," says Michael Gartenberg, a research director at market research firm Gartner. "If you look at Surface, it's an entirely different kind of device: the merging of tablets and computer in a new kind of experience."
The rollout also means Microsoft is looking to change its image, Gartenberg points out, innovating not only its products but how customers see the company.
"That's how you're going to judge the success of this: not necessarily by how many units of Windows 8 they sell but more importantly, how they reintroduce themselves to consumers," he says.
Microsoft Isn't "Cool" (Not That It Matters)
If Microsoft is revamping its image, it signals that the company's image needed revamping. According to Gillen, Microsoft's long-standing, widespread success did not make the brand hip and coveted in the same way that Apple is.
"I have to say that Microsoft lost the cool factor a while ago, and I think that Apple has successfully absorbed the position as the 'cool' vendor," says Gillen. "In that context Windows 8 has a pretty tall order ahead of it: restore Microsoft's coolness."
Still, being fashionable can only take a company so far, he adds.
"For the vast majority of customers out there, I'd have to argue that cool is not as important as functional."
Business IT departments, for example, care far more about functionality than fashion. Given Microsoft's willingness to let consumers adapt slowly, not to mention the fact that Office Suite is so widely used by schools and businesses, even the learning curve of a new interface might not trump users' broader comfort level with Microsoft's products.
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Danielle Kurtzleben is a business and economics reporter for U.S. News & World Report. Connect with her on Twitter @titonka or via E-mail at firstname.lastname@example.org.