"Is it better to lead the next level or be at bottom of the top?"

Unlike many parents, I couldn't care less about team's won-loss records - just want to see my son improve as much as possible before high school.

If my son plays attack (and midi to a lesser extent), I'd rather have his team lead the next level so there's more opportunity for him to work on offensive skills. If he's a defender, rather his team be at the bottom of the top so he gets more play action.

If my son was one of the weaker players on his team, I'd rather the squad be at the top of the division. Bench players get even less play time in losing efforts. When teams are winning, everyone gets playing time.