He is seriously mistaken. Of the many students I know/have known at even tippy top schools (HYPSM+), almost all of them were turned down by at least one other school at that level (ie, turned down by Stanford, but accepted at Princeton, etc.).
Esp at LACs, it’s not just (as students say too often on CC) whether student A is “good enough”, or whether student A is “better” than student B. It’s also about how the student profiles add up together to make a class, as well as institutional priorities that change from time to time. (from developing a profile as a powerhouse in subject X, to building a credible team in sport Y, to needing that tuba player, etc., etc.) and more. Swat does a useful exercise at the visit days*, where they invite parents to play AdComm with (anonymous!) profiles from real (former) applicants.The idea is to make tangible some of the many variables - including ones exogenous to the individual student- that are considered in the decision process.
Has he visited any of these schools / spent any meaningful time at them? imo, Swat & Brown are so different that I wouldn’t see any given kid being equally ‘at home’ at both. UChic and Swat might seem similar in some dimensions, but (imo) they feel really different (and not just b/c of the urban/suburban aspect). Being specific about the ‘why’ for each place may help with the focus. As for how many, ymmv but I have found that my lot had maybe 6-8 good ‘why’ essays in them, and the rest were kind of forced. For the highly competitive LACs, that essay matters.
*several schools do this- the Tufts version in their road show was a particularly good one