CACO - I'll answer your question a different way but ultimately the goal should be to maximize development / exposure. For some that may be on one of the best showcase teams (as the cream of the crop prospects), but for most its gonna be on the best team to maximize playing time and development.
One of the best comments / advice we got from Guerry Baldwin @ ECB years ago was.... If ya ain't playing, your not getting better - and everyone else is getting better around you. Doesn't do much good to be the 6th outfielder on one of the top teams in the country if ya barely leave the dugout. Another one of my sons former coaches would tell us.... It's about the journey, and where ya end up (versus this years team). Those pieces of advice have really helped to guide my son thru the years/teams.
At the younger age groups - have fun on the best team that you can find while making sure your son is challenged, developing and learning to play the game the right way.