It was a combination of the kids’ personalities and their parents preferences that shaped the decisions. For #1, who applied to some large public universities, some small private universities, and some small colleges, the set of colleges applied was determined largely by his parents. He made the ultimate decision to attend UChicago. For #2, who applied only to art colleges (plus Carnegie Mellon), it was her strong preference to find a college that was located in what she called a “real city” (preferably in the East), that led to her enrolling at RISD.
I don’t think “personality” had much to do with the decisions. Just preferences about the location and the qualities of potential classmates. In #1’s case, he wanted “a college where it’s safe to be a thinker.” To me that meant any number of liberal arts colleges including my alma mater (Reed). Chicago was perfect for him because it has an intellectual focus yet offers all of the advantages of a location in a large, “major league” city. But #2, while only applying to art colleges (with CMU being a hybrid case), it wasn’t personality as much as it was a desire to live in a city in the East that drove her search. Providence barely qualified, but its location allowed her to make frequent visits to long-time friends who were enrolled at NYU and Columbia.