Update Jan 2023 - S has 1 term under his belt now. Loves everything about the experience - classes, professors, weather, classmates, baseball. Academics are no joke - told me after the first week that there's a 50/50 chance he graduates. But he has it under control now and got great grades first term. He lives in a triple with 2 other baseball freshman and this has turned out to be critical for their success - academics are a team effort at Caltech. Problem sets are way to hard for any one person to figure out. I've heard about many night where 15-20 people are in his room working on Physics problems sets until 3AM. They're also having a lot of college fun but academics are def the priority for everyone there.
During the fall, he was largely on his own baseball wise. We'll see how the season goes - 6 day a week practices start next week and games shortly after. They only play 3 games/week so season stretches into late April. Roster size is pretty small (24 with 8 freshmen) so most everyone is likely going to have a chance to contribute. Perfect decision for him - I've never seen him so happy!