Meats,
I think it is important to understand with your post that most do not consider the HS season of primary importance.
Not that is should or shouldn't be that way, but recognizing that summer baseball has become what a player will attach his talent identity with.
Also, in your post you reference in which your son made decisions on what was best for him personally. Such as reps needed ect. So do those players who are considered the "cream of the crop". Most want to play with and against what is considered the best at their age level.
I am not sure what would be better. To have a select few teams in which consume most of the top notch players or to disperse them among more teams added with other talents.
Certainly, seperating the upper tier would reveal the true coaching abilities of some.
Possibly, I could see more competition created with the latter theory.