The article makes it pretty clear

> It’s not that I can’t afford to help him,” Steve told me. “I just have a real problem with handouts. And I want him to have the satisfaction of knowing he’s built something himself, with his own hard work. That’s how I was raised, too.

So it has nothing to with the son, Steve is just looking to validate his world view. The reality of the situation is that the boomer generation was provided with an immense amount of social assistance, affordability, and opportunity. Yet these are the same benefits they deny even their own children in favor of sadistic fantasies.