Although Pokemon is pretty sub-par when it comes to deep commentary on just about anything, what are some character or plot events in the games that gave you a different outlook of said character or the game's plot as a whole?

For me, I always saw Professor Kukui's introduction of Mount Lanakila as a sort of pivotal character moment when it comes to his ideals on battles. Alola has a VASTLY different traditions and customs that separates it from any other reestablished region (Like their disdain for trainers riding on flying Pokemon that aren't Charizard, seeing it as a bad omen). Their island challenges and love of Pokemon battles never really originated from sport but were more about appeasing the island deities, The Tapus, that helped protect them from the Ultra Beasts years ago.

Once you take that into consideration, Kukui's idea to "modernize" their customs with the ideals of the outside world becomes a bit disgusting, well, at least to me; He doesn't truly see the difference between the island challenges of Alola and the Gyms from his homeland, Kanto, and thinks of them having the same purpose of finding out who the strongest trainer in the region, when really, Alola traditions on battling were never about that.