Using the ultra wealthy who can buy their way into (or out of) anything is not useful as a point of comparison, because the percentage of people with that much wealth and power is very very small, thus yet are exceptional cases, not representative ones. The more insightful comparison is between the average high functioning middle class family and the average lower class low functioning family. The differences in behaviors, family norms, routines, etc. between the two reveals why this is sometimes intergenerational and lasts for many generations. Giving poor families more money or excusing them from paying for things does not address the fact that their family dynamics ingrain dysfunction into the children, who will repeat the patterns later. And yes, obviously this puts them at a profound disadvantage, but there's no way to stamp that out with welfare programs. Changing ingrained learned dysfunction has to come at least partly from within them somehow. Society can offer some forms of help but there is a fine line between help and enabling, and our society is too far across that line toward the enabling side, in my opinion.