You're totally missing the point of what Kanto tried to do.
The entire point of the pity badges was that they didn't feel earned in a way a gym badge should be. Every time Ash was handed a badge, it inflated his ego that little bit more, to the point where he believed his own hype. As the audience, we know he's not all that, but Ash doesn't (it's a cool little thing called dramatic irony). Doing this sets-up a big fall for Ash so he well and truly learns his lesson and then improves. They did this in the league because it was the most important moment in Ash's career to that point, therefore it has far greater consequences than losing any other fight.
In other words, it's basic build-up > pay-off. The pity badges were totally justified because they resulted in a great pay-off for the character.
They didn't do things as you suggested because Ash's arc wasn't about struggling to overcome things. It was about coming to terms with his own flaws and bringing out the good qualities within himself.
They didn't resolve the Charizard issue earlier because, again, it's tied directly into Ash's development. Ash doesn't know how to solve the problem because he's inexperienced and out of his depth, but he doesn't want to admit it. He would rather bluster his way through than admit his own shortcomings. Hence, it makes total sense for his character to gamble on Charizard obeying rather than sort out the problem.
Only when the problem comes back to bite him on the biggest stage does the penny drop. And when they lose again in the Orange Islands, Ash now knows he has to win back Charizard's trust and respect, and does so by proving he'll never abandon it - which also happens to be one of his redeeming qualities as a character.
Whether or not you like this portrayal of Ash is besides the point. Everything here is coherent and worthwhile.
Sorry for being so late in replying to this, but anyway:
Actually no, Ash actually still didn't learn his lesson even after his humiliating loss in the Kanto League, and that much is clear from certain OS Orange Island episodes. The effects of the so called great "pay-off" or development for Ash certainly were not evident in early Orange Islands. His arrogance, cockiness and inflated ego which the pity badges led to still very much remained. Like say, he knew that he still didn't sort out Charizard's disobedience issues, Charizard still didn't think of Ash worthy enough a trainer whom it'd like to obey, especially after that kind of a humiliation he suffered in the Kanto League, as a result of not trying to sort out Charizard's disobedience issues. But still, what he does in the episode
The Mandarin Island Miss Match?
Let's Charizard loose on a trainer's Tauros, just naively hoping that Charizard would suddenly obey him out of nowhere without him having to sort out the issues. Which makes it clear that Ash's inflated ego and cocky attitude still existed there, with him thinking that Charizard's disobedience issues would be automatically sorted out without him having to do nothing, expecting things to be handed over to him on a silver platter without him having to earn things legitimately via hard work and trying to sort out his shortcoming/mistakes.
Not to mention that he was acting arrogant and egoistic throughout the whole episode, having a high sense about himself after being on a long winning streak, and it requires a loss to Lorelei to finally bring him to his senses and develop humility.
So, in retrospect, Ash's pity badges and his totally humiliating loss hardly led to much development in the long term; it at best started the developmemt, but certainly did
not lead to any major development for Ash which made him immediately realize afterwards that he is supposed earn things himself, legitimately via hard work, things aren't gonna be just handed over to him on a silver platter, that he should try to sort out /rectify his own shortcomings/mistakes by himself, coming into terms with them. The so-called "pay-off" or development of Ash you're emphasizing so much on in order to justify Ash's extremely humiliating Kanto League loss and the laughable pity badges, didn't even happen much or come into effect that much as it was clearly very much evident in Ash's cockiness, arrogance and his egoist attitude in certain OI episodes like the one I mentioned, which happened
after the Kanto League BTW. If that humiliating loss in Kanto was supposed to be such a "big fall" for Ash which would then lead to a great "pay off" for Ash, making him realise his own flaws and coming into terms with them in order to bring out the best within himself, like you are saying, then why did all that arrogance and inflated ego as clearly seen in some OI episodes, still clearly very much existed, after the Kanto League?
Ir required some further harsh losses in OI to make him realize that he has to earn things himself, via hard work and and working out his shortcoming/mistakes, things aren't gonna be handed on a silver platter to him, and made him develop humility. So the pity badges and his humiliating loss in the Kanto League is very hard to justify in retrospect.
And well, since this thread is about which League was worse (whether it's in terms of narrative portrayal or quality) and we are all trying to justify an extremely humiliating loss, a loss where Ash was really embarrassed in front of a huge audience, consider this: As a trainer who competes in a high-level tournament like a Pokemon League, one is at the very least expected to command his Pokemon appropriately in a battle; because getting your Pokemon to obey you in a battle and commanding it appropriately is something which falls into the basics of Pokemon battling, and an entire audience got to see in the Ritchie battle that a trainer who is competing in the Top 16 round of a Pokemon League, can't even get his Pokemon to obey him and listen to his commands, which basically constitutes the basics of Pokemon battling.
If the loss is actually this much humiliating, I'd at least expect that it's effect leads to some really good development, making Ash realize the hard way that he has to earn things via hard work and sorting out his shortcomings and mistakes, things just won't be handed over to him.
We viewers all got to see a legitimate garbage League where hardly any battle can be termed as good quality wise or enjoyable, we hardly ever got to see Ash legitimately earn a badge in Kanto, all for what? What did we get to see in return of all the extremely underwhelming things happened in Kanto on the part of Ash? For that it leads some really good development later on, and makes Ash realize things the hard way, and makes Ash come to terms with his flaws and bring out the best within himself later on?
Then it may be justified......but, it didn't really quite happen just after all that humiliation/the big fall Ash went through/experienced in the Kanto League, Ash inflated ego and his arrogant/cocky attitude still remained, it just merely started the development at best. It's requires further harsh losses in OI like against Lorelei, like against the Poliwrath trainer in Charizard Chills where Charizard was brutally frozen solid, to make him realize that he has to earn things via hard work, sort out his own mistakes, he has to prove his worth as a trainer himself by all these, he has to prove himself as a worthy and good enough trainer to Charizard to get Charizard to obey him.
Merely starting the development, and not being the major cause of Ash's development (later proved in OI) isn't really enough in my book to justify those laughable pity badges and that absolutely garbage and underwhelming League with legitimate joke battles and and that extremely humiliating loss in there. If it was the major immediate cause, I can maybe still understand it that all off that underwhelming stuff that happened of Ash's part was perhaps really worth it. But nope, as proven afterwards, that certainly was
not the case.
So it's really not fair to justify Ash's pity badges and Ash's humiliating loss in the Kanto League by using that excuse that they were actually a part of Ash's development and to lead to a great pay off for Ash's character which helps him to come into terms with his own flaws and bring out the best within himself, because the effects of that so called "development" and "pay off" weren't really showing much just afterwards, Ash's cockiness, inflated ego and arrogance still very much remained after that for a sizable number or episodes as evident later on. It required some further remarkable events in OI which included some harsh losses, to make Ash realize that, he needs to legitimately earn things himself via hard work, by sorting out and overcoming his own shortcomings and mistakes. Those important and major events in OI, which made him realize that truth, were actually the key events here; the laughable pity badges and that extremely humiliating loss in OS weren't really much important in retrospective nor they were really badly needed either. The OI events which were the key incidents in developing Ash, could have been easily done much earlier, before the Kanto League without much problems; then Ash's Kanto League loss could have been of much better quality and could've been done much better as well, without this extremely humiliating/disgraceful loss even happening to exist in the first place.
