I run into a lot of people trying to target what a particular college is looking for (“I heard Dartmouth likes ambitious, outgoing leaders, so I want to write an essay that shows I’m an ambitious, outgoing leader,” for instance), but I’m very skeptical. Having known dozens of students who have gone to Dartmouth over the years (including my brother haha) and over two hundred who have been admitted, I can’t find any through-line like that. I’ve known shy, nerdy introverts at Dartmouth, brash, outgoing gadflies at Dartmouth, flaky creative types at Dartmouth, etc. Every college has a complex mix of students, and the notion that any school is looking for any particular qualities (other than the ones all schools are looking for) doesn’t ring true in my experience.
(One slight exception is Chicago, whose essays make pretty clear that it likes creative outside-the-box type thinkers. A soft heuristic for Chicago is if you read its supplement prompts and think, “this is going to be fun!”, Chicago might be a good fit for you, but if you read its prompts and think, “what is this nonsense?”, then it probably isn’t!)
(And of course Deep Springs is an even more special case!)