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The two initial screens that are relatively easy to do:
A. Financial. Run the net price calculator on each school's web site to see if it is likely to be affordable. If not affordable at list price or on need-based financial aid, then the reach/match/safety assessment must be made on the merit scholarships needed for affordability, not merely admission (an admission safety may be a reach for the needed merit scholarship).
As you brought up his orientation as a factor, you may wish to have him contact LGBTQ clubs at campuses of interest as part of the college search. Some posters have commented that small schools may sometimes lack a critical mass of similar people for support or eventually dating purposes in the future.
-LAC with small classes, seminars/tutorials would be great (although I’m not sure these are available in US). Big schools are out.
Your son has apparently determined that Williams is too "preppy/jocky". Yet he has reached the opposite conclusion about ... Colby ?? Colby would rank quite highly on most people's lists of "schools like Williams". People who apply to Williams routinely apply to Colby (which is slightly less selective) as well.