Well let me be clear about one thing first: I was never a true "fan" of Generation III or the Advanced Season of Pokemon mostly being that I was already a bit older, I'd grown up playing Generation II games (Crystal to be exact) and I was an old fan of the older Original Series of Pokemon. And in that token I'm not a big a fan of May either mainly because I didn't watch that much of the Advanced Series early on and I'd gotten Pokemon Saphire and Emerald Version later than anyone else at the time. What does that say about this picture for me? Well... I like it
Yeah I don't know May and Brendan all too well at all as characters but I somewhat got the gist of May from later seasons of Advanced and Battle Frontier but for me she wasn't all too appealing character wise. She just seemed into the Contests and a new traveling partner. But here May is-from what I get-like her game counterpart if she is your rival and a Pokemon Professor. That May I like much more than the anime to be frank and the way you drew may to be Professor like makes me think of her as a more impactful character overall. Here May is not the little contest girl you see in the anime, she's serious and somewhat playful adding on more to her personality overall but you get the feeling that there is more to her that can help you on your quest. When a piece can get someone to feel all of that from one look then you sir have done a great piece.