It is getting real late for baseball recruiting for schools that your son has not yet engaged. it’s around this time that my S went on OV’s to the first week or so in Oct. If he is a RHP and throws mid 80’s (low 80’s for a LHP), maybe some coaches will take a look. S had serious interest from UChic, Grinnell, Macalester and Carleton but declined because he was more interested in the NE and Cali schools (S was a RHP in mid 80’s but was also a position player).
If he is thinking of IB or consulting, for better or worse, there are definitely feeder schools where he will have better opportunities than others. A “Main Street” job in finance/business is less prestige driven. Even if he has missed the recruited athlete window, most academic D3’s have walk-on opportunities.
FWIW, D played at a NESCAC that was smaller than her HS. She had no problems finding her tribe socially or academically. Also if you are on a sports team, the tendency is that your teammates become your social group. S on the other hand felt the D3’s were too small and opted for a D1 school where he played Club baseball. It really is a balancing act and your S and you have to anchor what is non-negotiable (cost, size, location, academics, sport) and work your way through from there.
Best of luck.