My son has typically played little league and fills in the year playing on a travel team for a few tournaments in the summer and 2 or 3 in the fall. In little league he is one of the top players in a competitive program, all star teams regularly go fairly deep and have gone to state and region several times in the last few years. (our age group, 12 this yr, has been fraught with politics that have cursed the all star teams performance we have not made it out of district, my son has been picked and played on the team and is not as affected as others but the kids are smart and know whats going on)
This fall he played on a more competitive travel team, and made friends with a kid that is on another premier team in the spring and he really put the pressure on my son to play with his team instead of little league. He's torn, new friend vs old friends. We would have to drive 30 minutes farther to practice (each way) but they get to workout at the local div 1 perennial top 20 program and one of the assistant coaches there runs practices, they get to practice on the field and use the indoor facility. We went to one workout and the coaches want him to join.
To my son's credit he is asking me for advice, clearly he will face harder competition playing premier baseball vs Little League. He may not get to play the position of his choice all the time or bat high in the lineup, (thats an unknown really) but its an established team that has been playing together for 4 years and he is the new kid. A lot more games and travel, they do plan to go to Cooperstown, but also to several other states for tournaments as well.
I think he has time to keep developing his game and am fine either way but was curious if anyone else had advice, wishes they had stuck with little league longer, or has a strong opinion that its time to start getting ready for high school the sooner the better.