When should the series have ended?

[withheldforprivacy]

Forget commercial purposes and the needs of the fans for
the series to cover every new game. From a writing point
of view, when was it the best moment for it to end?
I think it was the orange league. Ash finally stopped being
a goofy trainer, earning Charizard's obedience, defeated
an undefeated trainer (Drake), won a trophy and proved
his worth. We know he'll never win one again, that orange
league was the peak of what he could achieve. All in all, it
was the perfect full cycle of Ashes growth and development
since he left Pallet with Pikachu.
I'm not saying we shouldn't have had Johto/Hoehnn etc
seasons, but it should have been with new protagonists.

 

[Captain Cadaver]

Either Orange Islands like the Pikachu Denki manga due to Ash having won a league, or have Ash's main story end with Johto due to the resolution of Ass and Gary Motherfucking Oak's rivalry and have the series cycle through different protagonists like the Pokemon Special/Adventures manga.

 

[Fantastische Hure]

Probably Johto, in my opinion. Make some changes and maybe cut down on the filler a bit.