I agree that “find a way to finance it” is not a desirable strategy. If the money were sitting in an account waiting to be used for college, and the parents are fully funded for retirement, then sure, full pay at Midd makes perfect sense. But parental loans or borrowing from retirement accounts etc. to fund Midd vs. no debt for St L or VT Honors does not sound advisable. St L for a motivated student could be a terrific experience, I believe there is a semester in NYC for Econ majors with the ability to intern in finance. VT honors would also be a good option. Research career outcomes at St L and VT, ask Admissions for people to talk with in Career Services to get more specifics about interning, alumni networks etc.