This is one of the problems with socialism for me, speaking broadly - it can't distinguish between individuals, and so has to lump them together for the purposes of distributing "fairness". Because spurs 4 life doesn't fit into Whiskey's model of the poorly educated, it's irrelevant to his thesis. The fact that people from identical backgrounds are capable of achieving such different results is aggravating to those who'd like to do broad social re-engineering, as it kind of pisses on simplistic views like "oh, it's a lack of good education that causes poverty, therefore better education=less poverty".
That's not to say that the thesis doesn't have merit - there's undoubtedly a link between education and poverty, but it's not a simple analogue.
I've never suggested one size fits all approach anyway. Nothing is a given, but it's all about chance. I've never said you can't achieve if you come from a poor background, just that your chances are a lot lower.
What is really frustrating for me is that people who have come from a poor background and have broken away from it seem to forget that and instead of trying to help people from that background just say 'well if I can do it, anyone can', when blatantly that is not the case.