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If we look at characters individually, then it's easy to say "oh yeah the writers can give them whatever personality and interest they think fits." But no character exists in a vacuum. They have to be analyzed in the context of the universe they are placed in as well as how they and their respective show fit into the real world. This is where we start seeing patterns, and the patterns are where the issues lie, not so much with individual characters (for the most part that is). On their own you can easily argue any of Ash's female companions are fine characters and that their goals are ambitious and compelling. But when you lay out all 5 of them (Misty, May, Dawn, Iris, and Serena) you see the patterns of none of them challenging gyms like Ash, none of them really being as battle oriented as Ash in general, 3/5 of them participating in the 'girly' option involving performing and dressing up, the list goes on. Zooming out slightly you can also see that Ash has never had a competent or consistent female rival, and most of the strong, anime-exclusive trainers he meets are men.
In response to Muur's comments, the anime writers aren't responsible for the champions, gym leaders, or any other game canon characters. I don't think it's fair to say the anime is excused for the patterns it introduced just because it didn't change decisions put in place by another party. Plus we never saw those champions fight through the league on-screen. They had an opportunity with Iris where they could have had her goal to become champion, like she does in the games, but instead they gave her the vague goal of becoming a "dragon master."
Also I think that having a female winner, or even top contender that gets screentime, is important. If the only awards the female characters ever get are things like top coordinator, but the focus of the show is always the battles, then you're really sectioning off who is meant to fill what roles. It's one thing to try to appeal to your target audience, which the games seem to do fine with their mostly equal representation. But what the anime does is tell its audience what they should be interested in rather than letting them find their own interests organically.
And there be the problem. No matter what series he'll be in, Ash always occupies the main player's goal as he is the main protagonist of the show. Could the girls partaken Gym Battles and fight the League? Yes, of course. But it creates a redundancy as those female trainers will have to battle the same Gym Leaders as Ash, and it will get repetitive seeing two of the same Gym Battles at very least. And unfortunately, that's why I have difficult time answering the question: Why can't females win the League?
Because this is ultimately Ash's journey and we the audience want him to win the League tournament even when the executives constantly deny him. And Ash has gotten to the point where he could easily reach the Final Round of the League if he really puts his mind to it. Simply by that, the thought of making him lose just to allow another trainer to win for once is almost unthinkable when he has no victory to claim for his own. By this point, people have become cynical about the League tournaments. It does not matter if a girl or boy wins the League, because if it's not our 20-year old main character, there is no interest to stick around.
I remember my thoughts when the Kalos League was near. I had no desire for Ash to get another Top 8 or Top 4 again, and have someone else win. I wanted Ash to win because he has shown himself to be at his finest and most experienced yet. And that, unfortunately, overrides my desire to see anyone else win.
It would be nice if Ash won the Kalos League, and next series features Moon as our new main protagonist competing for the Alola League.