1. Marketing to the 'cool kids' with the expectation that everyone else will follow-along... is probably not good advice in the absence some key differentiation. For Microsoft, this could have just been the massive amounts of capital they could deploy towards getting the Xbox to market. Even then, just spending money is not a strategy.
2. Middle-aged IT people are likely to have more disposable income to afford a $X00 device and a library of games (where the real revenue is). They could also be thought to have less leisure time and place more value on it accordingly, which would correspond to spending decisions. They may also see themselves as 'skateboarders with tattoos.' There's nothing demographic specific about those properties.