When I first asked this question I was thinking mostly of gym leaders, but I'm so glad to see the creative ways that this experiment has gone. Now then, as with all good questions, it would be unfair for the asker not to answer their own question. Thus, with the way things have gone, I'll answer with both my original answer and my new thoughts taking into account all possibilities.
Original:
·Winona- a young prodigy with her eye on the ball. Winona's a bit serious for her age and shows little mercy. She would provide quick decisive attacks with a variety of high flyers. She's the first only relative to the others.
·Morty- a patient man that knows how make the most of what he has. Kind to anyone he meets, Morty is the voice of conscience of the group willing to take hits for others. He would be strong with afflicting conditions and immobilizing enemies while being elusive. Maybe he's the second in line but he's tricky.
·Blaine- a wizened man able to find a way to cheer the most depressed of people. Lighthearted and energetic, Blaine is a morale booster. In battle however he is a clever old man. He knows battles like the back of his hand and has had time to perfect his strategies. He won't be easy.
·Volkner- as serious as they come he won't stop until the job's done. While he doesn't seem it, Volkner is passionate about Poke'mon and is determined to solve the crisis at hand. As a battler he is a genius. Where Blaine has wisdom stored up Volkner naturally understands battle and his high energy hidden beneath a lax demeanor makes him dangerous as an opponent.
New team in another post.