>>40552002fp as usual, bp, thing is that very few characters in Pokemon actually have personalities, there's nothing usually said about their occupations or their personalities, there are exceptions obviously but they're few and far between. The sidequests in Gen VII were a novel concept, not the first time the series has done it either although like you said they're pretty boring, if they wanted to make them more interesting they should've made them include something engaging for the player whether that's some sort of side activity or a quirk on the battling system. I think the Masters in LGPE was an interesting concept but only really for one trainer not 100+, if they made a single trainer who would mirror the player's team in Pokemon and levels with specialized movesets for each Pokemon I think that'd offer an interesting challenge, an opponent who is highly adaptable.
