Very simple answer IMO. You don't really talk about your son's thoughts on this matter other then mentioning that he likes current school. As a HS teacher/coach, I have seen far too many transfers take place because parent talked or forced student-athlete to transfer. In most cases it does not work out for transfer. Definitely exceptions with good example being a local (Colorado) pitcher, Cole Winn, who transferred out of state (was at a 4A program in a 1A-5A classification system) to CA and Orange Lutheran HS. He was recently drafted with pick 15 on day 1. IMO, no way he has that kind of success without demonstrating that he could dominate some of the best HS competition at the highest level! I think this is rare which is why I would educate your son about what you believe are pros/cons, working hard not to influence his decision. Then let him decide!