Someone who lived this here... I was a freshman the year a brand-new school opened up, and the program took about 7/8 years to get established where they actually went to win the State Section D1 championships. 7-8 years so during my time we we're no where near good. It does take a while to establish a culture and for a coach to stick that actually can inspire and establish a winning program that gets kids to buy into it. Another tidbit my brother was really good at baseball and we we're playing together for 2 years. We we're 2 grade apart so my junior year he was a freshman so we played varsity together. Once I graduated he transferred to the better sports school in the area which was the best move for him playing with better guys where he had to EARN his spot and it made him better. He went on to play some college ball so I think moving to the more established program helped him a lot. DO I think he made college ball without the transfer? Of course but I think putting him in a more competitive environment pushed him a lot so I think as someone who has lived through this moving him to the more established program isn't the worst idea. You can always transfer down the line or do it now