>>26555816Because it's a series aimed at young boys.
Yes, many of the main characters would be likely to suffer some terrible failures early on. But they'd all eventually grow into champions.
Ash is a perpetual loser simply for the purpose of ensuring his journey never ends. Can't keep the series running if he attains any form of mastery, therefor it must forever be unattainable to him.
You eliminate this problem if you change characters every gen. Your main character is allowed to win, allowed to attain mastery, because while his journey may be over, another will begin anew with fresh blood.
Which, again, would keep the entire formula from going stale.