Regarding Cosby's remark about black families, I certainly understand his sentiment, but I agree it was somewhat simplistic. My father (and my grandparents) all had a pretty similar view to Cosby's. In the particular black neighborhood of Philadelphia where he was from, that type of conservatism was the norm. By the early '70s, several of his friends (along with him) had graduated from college and moved out of the cities into the predominantly white suburbs, and this cohort was for the most part extremely successful. Not everyone managed to get out of the city, though, and it wasn't because the ones who stayed behind were necessarily lazier or less hard working (though certainly many of them were). For the most part, the opportunities just ran out.
With that came, I think, a lot of the anti-assimilationist sentiment you see today. Yang mentions something similar in his article. When you work your ass off to excel in all of the culturally approved ways, but nonetheless you are passed-over for someone who worked half as hard as you, what are you to think? There's a whole generation of older black men who were stung in this way (and, as Yang mentions, a whole generation of Asian men in a similar, but largely better, situation). (And incidentally, I'm speaking about men instead of women because women face different challenges that I'm not qualified to discuss). In many ways, I don't think the situation is much different than what lead to hooliganism in the UK during the '80s.
So is the situation getting worse, better, or staying the same? Economically, it's a hard time for a lot of people. Kids graduating from college (of any race) are having a hard time finding jobs. Thirty-somethings who saved up to buy homes in 2005 are underwater. As global inequalities are being addressed, global competition is at its highest, particularly for jobs that previously would have been "entry-level". These are also the sort jobs which are most prone to nepotism.
Its hard to say what lessons will be drawn from this period. It seems entirely possible that many of the hardest working, most optimistic young black people of this generation will find themselves out of work, disillusioned, and wondering why they didn't just have more fun in high school (and passing that attitude on to their kids).
BTW, you might (should) say "Don't Asian Americans face the same economic difficulties? They're employed at the highest rate of any ethnic group in the country." This is true, of course, and there's a lot to say about that. But I think this post is already too long, and none of this has been particularly relevant to hacking, except maybe societal hacking. Maybe I can end with a question: why don't white kids, generally, work as hard as Asians, especially when they are being out-competed for valuable educational opportunities?