When a Cub Scout moves up to Boy Scouts, he will naturally have moved into a new school (High School vs Elementary). So instead of just transfering him, you would need to change his school designation, too.
Doing the recharter would be a bear. We already have regular youth, and prepaid youth (those who signed up at school nights) and now we would have life time youth at a different fee amount? How would scoutnet be able to figure the amount to charge? Plus, some boys lose interest in scouting and would want a pro-rated refund. And how would his fee be transferred when he moves to Boy Scouts or a different council. I see more problems then benefits.