Ok here's my idea:

You know how I'm drawing myself as a harajuku Fairy type gym leader? I think I'll make Anny some kind of backstory or something. I imagine she started off as a bug catcher and had a bunch of cute bug Pokémon- maybe a Caterpie, Sewaddle, and Cutiefly. She loved Cutiefly the most, and she eventually switched over to specialize in Fairy types. She goes through the gym challenge in her region (to be named later) and the champion (to be named later) recognizes her talent and asks her to be a gym leader.

(Some of the gym leaders in the region will be the other gym leaders based on me)