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I've got a solid solution for the Anime.
Have Ash Personality Arcs.
I think, from BW onwards, we could have some arcs focusing on the wrongs of Ash's current personality, and his focus to improve those faults, and continue in the next Region.
For example- After having a high rank in Sinnoh league, Ash would've gone high-and mighty and thus incompetent. And after having a comparatively low rank from Unova League, Ash would go into an arc of self-realisation, getting his faults, and his lack of focus that led him to lose the Unova League.
Then, he would carry onto Kalos, as a more modest person at heart, and his modesty leading him to catch stronger Pokemon, have more development, and thus be the runner up of the Kalos league.
This would seem more believable, and would make Ash more bearable as a Character, it would also be relatable to children, and their schools, as one year, they get more marks, another year, they get less. But in the end, they strive to be perfect. One Grade as a 'Region', Exams as 'League' and all the rest.
One perfect example in Pokemon anime was the Ash-Greninja Arc, with Ash reviewing on his (then) recent losses to Sawyer and Alain.
Have Ash Personality Arcs.
I think, from BW onwards, we could have some arcs focusing on the wrongs of Ash's current personality, and his focus to improve those faults, and continue in the next Region.
For example- After having a high rank in Sinnoh league, Ash would've gone high-and mighty and thus incompetent. And after having a comparatively low rank from Unova League, Ash would go into an arc of self-realisation, getting his faults, and his lack of focus that led him to lose the Unova League.
Then, he would carry onto Kalos, as a more modest person at heart, and his modesty leading him to catch stronger Pokemon, have more development, and thus be the runner up of the Kalos league.
This would seem more believable, and would make Ash more bearable as a Character, it would also be relatable to children, and their schools, as one year, they get more marks, another year, they get less. But in the end, they strive to be perfect. One Grade as a 'Region', Exams as 'League' and all the rest.
One perfect example in Pokemon anime was the Ash-Greninja Arc, with Ash reviewing on his (then) recent losses to Sawyer and Alain.