1) Why would a family choose to live in Stevenson's district? The taxes here are far and above that of surrounding areas. For example, a $649,000 house in Long Grove might have to pay $16,000 per year in real estate taxes plus $1200/year in home owner association fees such as this house:
If all it takes to succeed in life is to try hard, why would anyone want to pay so much extra for a house that is the same size as the less expensive one? The reason is often because the house comes with so much more than living space: a higher achieving school district, a lower crime neighborhood, neighbors who have similar values to you (such as do well in school), lower pollution, etc... All of these provide an advantage to the children growing up in that area. I am not not saying that the advantage is wrong or that anyone should feel guilty for having that advantage. I simply want to acknowledge that the advantage does exist.
2) Try to objectively look back at your family's rise in social class and see the dynamic that fueled it. Did your parents value education? Why? Where did that value come from? What if your parents were born into a house where they were told that school was never going to help them? Did your parents have parents at home to help them? What if one of their parents was incarcerated for most of their life? What if their parent was addicted to drugs? Were your parents raised in a neighborhood in which they were subjected to violence? Did they ever know someone close to them who was murdered? How might the daily threat of violence affect them growing up? How would they be shaped if they were forced to belong to a gang simply because of where their neighborhood is located?