Little League Baseball Question

Question
Hello,
My son is going to be playing U8 baseball next season.  This will be his 3rd season of Coach Pitch.  He loves the sport and asks me to play outside just about every day he doesn't have an organized practice or game.  We play catch, I hit him grounders & pop flies and then he bats.  He has developed into one of the top 3-5 players on a good AA team, primarily because he practices on his own so much.  There is talk that this team may split next season so we may be looking for a new team.  I am not a coach so the odds of him getting to play much infield on a competitive team are not very good.  Those spots seem to be mostly locked up with coach's kids. For his development, is it better to let him try out for a really good team with good coaching and good players, even if he has to play outfield all the time, or is it better to find a team where he's noticeably better so he gets to learn an infield spot.  To date, he has played mostly outfield and he's good at it but I just want to do the right thing to help him grow into an all around player.  My gut tells me that playing with the best players and coaching will make him the best player he can be regardless of position but I just want to get some confirmation on that or a different opinion if I'm off.

Answer
Hey dad,

Playing on a good team is always a good thing, but not if he is gonna sit on the bench most of the time.  Go with the better teachers and someone who thinks that he will be playing regular. Talk to the coach about your concerns.. At his age, isn't it better to play on a little less of a team, than sit on the bench and watch others play and wonder why not me?  He is still at an early age, and things can change from year to year..
Take the team that will allow him to play numerous positions, and a team that will not shut him out.. Sometimes that can be the team with less (coach's sons) on the roster..
It is better to be the ninth kid on a good team, rather than the eleventh kid on a great team. And sometimes, that great team, loses it's focus on being fun..
Good Luck and keep me posted..
Dennis