>>55389764If the destination wasn't "beating the strongest trainers in the world" there would be no problem. The Masters 8 just sticks out as one destination that really, really shouldn't have happened.
Every other destination was perfectly fitting. Ash coasted in OS by relying on powerful pokemon he didn't train or bond with, and it ended up coming back to bite him when Charizard refused to carry him. Ash became a better person in GS, but didn't improve as a trainer much and ended up losing again.
That he kept abandoning his pokemon every generation made it more believable, since he wasn't giving them the chance to gradually improve over time. Understandable, since the anime has to shill new pokemon.
This trend that continued in every generation(ignoring non-leagues like the Orange Isles, BF, and Alola) up until JN where he was suddenly put on the same level as champions. It ruined it the flow.
Ash should have stuck with Goh and joined Project Mew, and his grand retirement could be catching the same pokemon that kids back in the RB days were obsessed over. Anything but the Masters 8.