It comes down to what you want to do. Is your son close with the kids he is playing with? We had the same core group of boys starting at 8U select. A few came and went. We knew after 14U that my son was probably going to be a D1 player, and probably one of the few on the team. We had a talk about moving to a power team but he was really against it, as he wanted to be with his friends. Our plan then focused on showcases, so that he could prove he could pitch against top talent. I would say we have no regrets. Some of the best summers as a family, we have ever had. Siblings had grown up together, the parents all got along, and the boys are best friends. 15U and 16U, we did start to get scouts at our games to watch, but most of our recruiting process was built on showcases/camps. You just have to decide which path you prefer. The showcase path is a more hectic schedule, trying to fit them in around travel ball, and more expensive because there are a few you really need to do. If he isn't especially close with his team, 14U, 15U is a good time to break.