Microsoft has figured out how to advertise - they show real people doing cool things with Windows, and how easy it is. Apple has been pushing that line for years - and while Microsoft has caught up in a lot of ways, they've let the "Mac is easier" tag stick for way too long. The latest set of ads, where they have kids (the one I just saw had an 8 year old) doing things like photos and movies are great stuff. Way, way better than the Seinfeld/Gates silliness they tried last year.
This all gets back to something I dislike in current marketing fads: story telling. The first set of Gates/Seinfeld ads were all about telling a story, but they were utterly disconnected from the product being promoted. The new ads also tell a story, but they tell one that promotes the product in question. As I've said before, connected stories work. Disconnected ones don't. Unless you tell people what kinds of problems your product/service can solve, you're not telling a useful story - no matter how many people hear it.