I'd say it's time to have him start attending other try-outs and see if he can handle tournament teams with top kids. Mix it up a bit and see what he's made of.

By mid-squirt years, outside skills coaches become a valuable ssset. The team can only do so much. If you feel good about your kids development, I would say it's time to begin working with outside people now. They should give you a decent assessment of your kid's ability.