Microsoft owns 95% of the world's desktop computing pie.
So ? That's great and all but, is Microsoft COOL ? That is the BIG QUESTION HERE. Because when it comes down to it, most(on a global scale) people/business run Windows because they don't have a choice. Apple is a good OS but, too limited (depending on what you do) and not cheap, and PC's are cheaper so most of those people get a Windows computer because of bang for the buck and they can do what they need for the most part.
Then the other side, as said above, the term Windows refers to work, not fun. AKA=Not COOL.
They would have to look at people in the 16-18 year old range (young, starting first jobs, fairly hip to modern music and trends). If you asked then what they would want, a Windows Tablet or an iPad, what do you think they would say ? I would almost bet by a very high margin that they would say an iPad. Why ? Because it's cool. The Windows Tablet would see limited on younger minds because their parents use Windows and they want to be different. This is why these devices are so successful. Android is trying to get on that market and the only way they can right now is with a $59 tablet (very low prices)
When it comes down to it, these are the demographics that Microsoft should be going for with their ads. They might not buying today but, when they get jobs and get fairly good income in a few years they will be buying. They are the next customer and where they should be targeting.
So their ads need to be more edgy, more perky and more HIP to modern trends. A lot more edgy than they are almost on the line of being offensive.
For me, they just need to put Windows Media Center in Windows 10 and you got me !