Not an entirely unique situation, but I do extend empathy to his family. I have more than a few friends in NYC, who are stretched thin, despite on paper looking like they are doing relatively well (300-500K salary) and equity in a coop. But, after NYC private school, a mortgage that in many instances, is at least 5K, and more than one child in school, well, sometimes the math does not add up in a practical sense.
Speaking personally, we are paying full retail at an Ivy and OOS UC, and that is in the low six-figures annually. Writing those checks never become easier…