If your looking at the program for the long term then you need to consider your son will be in HS in a couple of years and you need to find a team to meet those needs. If it were I, here is what I would be looking for:
-Play at grade level, don’t play up, and don’t play down. This becomes somewhat important when you get in HS and start playing in showcase tourneys.
-Find the best team you can where your son will get the most playing time. It does not help anyone at your son’s age to be sitting on the bench. He needs playing time to improve. Conversely, don’t play on a team that plays against teams below his skill level. That does nothing to challenge him.
-Find a program that is not known for daddy ball. I don’t really care if a father coaches my son’s team but they better not be favoring their son if he is a lesser player.
-Decide what you want out of the program. Do you want a program that works with the kids in the off season on things like strength and conditioning, batting skills, pitching skills, etc. Or do you want a team that expects the kids to learn those skills on their own.
-If looking at the program long term, find out what they do to get the kids exposure. A lot of programs say they do this, but many of them do not. I’m not talking about playing in the fall PG event. Or going to the Under Amour showcase in July. I’m taking about a program that plays in front of college recruits and scouts more then they play in tourneys. I started a thread about this a week or so ago. We have two weekends left in our season and are playing our first real tourney this weekend. Everything else has been “showcase games”.
I’m sure there are a lot of things I am forgetting, but these are what I see as highlights.