If he wants to go JuCo to D1 don’t just go to any JuCo. Go to one with a reputation of being a feeder to D1 ball. Research where the players go D1. Typically it's where the connections are.
But if the kid isn’t a D1 talent now there has to be some introspection on why. Is he a late bloomer or just doesn’t have the talent? Talent isn’t going to just appear out of nowhere in the next two years.