Thanks for all the great thoughtful responses, what a great forum to join!
For some context ... we live in the SE PA not too far from Philadelphia and near the intersection of PA, DE and MD.
I'm not at all worried about my son's transition to the big 60/90 field, his 7th grade school team played 60/90 last spring, and he did fine. We kept him in 12u this summer as we knew he would have a ton of fun (you are only 12 once). We recognized that playing up 13u summer travel would have been better for his development, but also knew that being a kid for one more summer would leave him (our family) with some priceless memories we shared with the other baseball families we have been with for three years now.
To find the balance, we also took him on a couple far from home baseball events that would push and challenge him, to gage his ability against some nationally recognized 12u peers and also against some older middle school kids on a 60/90 field for a week. The better the competition, the more locked-in my son became, and his raw abilities stood the test. Now, as parents, we are looking outward at his grad year cohorts, many of these top grad year performers are more than 12 months older (you know those red-shirt first graders ...) - and we are asking ourselves how best to put our son on a path where he can catch up with the best 2024 grad year kids (without regard for their birth age).
The heart of my question(s) is to find balance in the journey forward; and to seek well informed advice that our family can include in our decision making. My own baseball journey ended in high school back in the mid 80's. So, I know one thing … is that I do not know any of the answers to these questions.
1) How to maintain a proper balance? - my son who has always played sports for the pure joy of it and for the spirit of the competition - did not care what sport he was playing as long as he felt he is competitive. I know if we push to much - too hard on one sport, he will burn out or eventually resist it.
2) How to know when it is time to move on from his current travel team? - if we leave the current program, our son will miss his friends, I will miss my adult friends. The current program is small while being regionally competitive, conveniently local, and nicely affordable. But, we also know staying with his current team will stunt his individual development.
3) What does it really mean to "seek out the best competition" and "play for the best team you can play on" ? - how should we help our son decide to either join a recognized 13u team with half the roster in my son's grad year and is at a PG tournament every other weekend ... OR join a local 14u team with the roster of all older kids but may not be as successful or may not travel as far to seek out the best competition in their age group?
PS: Very much appreciate the attention on academics!