For my kids, being in the middle of Iowa would have been less than ideal. And Oberlin has its own political flavor that might put some kids off (although I’ve noticed this year some other schools “catching up” in that area – topic of another thread, though). Honestly, we made a decision somewhat like the OP’s for both kids. One kid took the merit. One took the higher priced school. Both had great experiences that worked for them. My guess is that Midd would have won out for my kid, especially if they were foreign language focused.