I agree that the decision will have to be one driven by the fit of the college to the applicant. Both financial fit and environmental/academic fit. Things are very much an individual choice determined by the uniqueness of that particular individual or familial circumstance.
As for our family, my D would have been miserable at Princeton. And we would have qualified for no financial aid there and of course the Ivy League offers no merit. Everything that she read about Princeton made it clear to her that this would be a terrible environmental fit for her. The last piece of information about eating clubs made it the last nail in the coffin. Not that she would have gotten in. But she was looking at all possibilities.
On the other hand, the more she found out about UChicago the more interested she became. She initially was not looking into going to a school in a big city. Also, UChicago is still one of the few offering merit scholarships. So that was definitely enough to put it on the list and apply.
It seems presumptuous to just say"Princeton. No contest". There is more to consider than just having bragging rights to an Ivy League application/acceptance.