Lauren Fichter and her husband earn about $350,000 a year. The couple own their Reading, Pa., home and a vacation property they rent out on Airbnb. Their three children play club sports, and the family often grabs takeout after games. But when her son Dalton heads to college next year, he’ll have to tap student loans and hunt for scholarships. The couple haven’t been able to save enough to cover all of their children’s expected college expenses, which often cost around $75,000 a year per student for families at their income level.