just my opinion, based on experience with my June birthday HS class of 2024.
1. get on the 60-90 field as soon as possible, so play up ... as long as it is playing and not watching.
2. play games and train with older, bigger, and better players as much as possible
3. then, when he enters (or is sucked into) the college recruiting process,
play in exposure events with kids in the same HS graduating class
4. let your kid decide on 1 & 2 above.
My son has played in 5 different age groups over the past 4 calendar years: his baseball age group, his grad year group (2024's), grad yr -1 (2023's), grad yr -2 (2022's) and in a local adult league. During events/tournaments considered to be "college recruiting events" he was playing in his HS grad year group or 1 yr up (never played college scouting events at his baseball age group). Note, there were days he thought playing back down into his baseball age group would be fun (winning with friends is fun) ... it took some time to cut that cord completely.