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Some thoughts on Ash's progression
>RBG
Nowhere capable of defeating the toughest gym leaders. Charizard refused to obey outside of Blaine.
>OS
Ash progresses greatly by gaining Charizard's trust and becoming a much more competent trainer. By defeating Drake he proved his ability to defeat the strongest gym leaders.
>GS
Depended a lot on his veterans resulting in his newer mon being weaker. This caused Brock and Misty to call him out so he gradually tried to rely on vets less but still ultimately used his veteran pokemon more. He lost to a more experienced trainer but was clearly a capable League-tier trainer.
>RS
Ash took into account the advice of others and started anew, showing progressed maturity. We see him rear a new team so capable they could match Tyson, who won the Conference. This shows Ash's improvement and shows he is capable of winning League Conferences.
>BF
Ash used a mixture of new and old pokemon to show his skill as a trainer to take on trainers said to be comparable to the Elite Four. By the end of the challenge you could argue Ash is nearing E4-tier
>DP
Ash starts anew again but has a rival with equal experience. We see the progression of his skills, techniques and power to the extent his newer pokemon manage to defeat Paul, who used veteran pokemon and then defeat not only Darkrai, who swept Sinnoh, but also Latios when the finalist facing Tobias could not. You could argue Ash is Low E4-tier here, being far more powerful than trainers capable of clearing Conferences.
>BW
No.
>XY
He rears a team capable of rivalling a trainer who defeated an E4 in a battle that could have gone either way. He is firmly E4-tier.
>Alola
He defeated Kukui, a trainer who beat the Kanto E4 (at least in games lore) and Tapu Koko, a legendary far surpassing Latios, with Pikachu. There is no doubt Ash/Pikachu would stomp DP Ash/Pikachu even without Z-Moves.
Sub-8th Gym > 8th Gym+ > League > League Winner > Sub-E4 > Low E4 > E4 > E4+. A clean progression, surprisingly.
