You should go with fit. But I agree that Kenyon has a better academic reputation, at least historically. It is the most beautiful school I’ve ever seen. Just depends on your gut reaction and which school draws you more. Never been to Skidmore but people seem to like it. People who go to Kenyon seem to develop very close friendships and tie to the place. Probably also depends on what you are interested in studying.And reputation isn’t everything either; it sounds like you picked the right school based on fit and while it’s normal to second guess yourself, you shouldn’t!