Having just come out the other side of navigating the travel ball landscape I'll throw out some observations.
- A baseball academy is a small business that requires a great deal of management. In my opinion its very difficult for a person (or family) to both run a successful small business and also keep up on the very latest advancements in hitting/pitching. I've found that the best instructors don't really have much time for coaching teams.
- An academy can specialize on one side of the ball. My son played 14U for an organization that was very advanced on the pitching side (Driveline program etc.) and was woefully ignorant of the latest hitting philosophies.
- Academies have a lot of mouths to feed. Sure the top guys may have great contacts, but if they have 2 or 3 teams at 4 different age groups how much time do they have to make calls on your son's behalf?
If I had to do it over again, I'd first focus on getting the very best individual instruction possible. Maximizing that will make a player attractive to any number of teams. Then find a team where there is the right combination of playing time and high level competition.