This ad establishes two points very well. Firstly, Microsoft accepts that its product, and those of its partners, are perceived as being of lower quality than Apple's. Secondly, it knows how to use this perception to establish itself as the more reasonable choice for everyday people who don't need top-quality products, but who do have a strong idea of what they need.
Mike Arrington admires the line, "I’m just not cool enough to be a Mac person," but that's not the smartest part of the ad. That would be how its scenario takes characteristics associated with unsophisticated shoppers and presents them as evidence of pragmatism and a go-getter nature: unplanned and un-researched major purchases made under a manufactured sense of pressure, with up-front price rather than long-term goals in mind.