>>39496858Orange Islands are literally just 5 glorified gyms, with no tournament at all. Winning the Orange League is probably as prestigious as completing the Island Challenge, ie nobody really cares about it even in-universe.
Alola is shit for not having any requirements to enter the tournament, but at least it has a fucking tournament. It also has the excuse of being the first one of its kind.
But the main reason is: it was a different time. They probably didn't plan to stick with Ash as the MC for as long as they did. And between Kanto and Johto there wasn't even a "reset" like the ones we've been getting since Hoenn.
But at this point they need his character to be as malleable as possible. That's why he'll never get character development, never achieve anything too big, and never get a single step closer to fulfilling his dream.