I think it might be easier if it were a round point basis, doing a best out of three, so if the challenger wins the first two rounds, then they get the badge. That shouldn't happen too often, since battles are fairly even, doesn't hugely matter on the Pokemon. If you have type advantage and you go second on the last round, you'll be fine. The only disadvantage is issuing commands first, that's always screws people over, since the commands issued second are usually a counteract to the first.

Since it's Cynder's Gym, it's her call, this is a test after all. We can do a Espeon and Lickilicky vs Reshiram and Hydreigon if we want, first to KO. I wouldn't mind finishing this battle and calling it a draw though.