Oh, and I was thinking about the mechanics of the battle... and I don't think half and half is going to work. Because once the winner of the round with Skarmory vs. Joltik is over, one trainer will have a left over pokemon to use for the rest of the battle, right? Unless it's strictly Skarmory vs. Joltik and Croagunk vs. ???. Is that making any sense, or am I just crazy? XD
I'm happy to give your way a try. Nika's picked Spider, her Joltik, to go up against Skarmony. Do you have a preferred outcome for either Skarmony or Tristen's development? The type match up favors Spider (slightly) but Skarmony is a higher level, so either outcome would be plausible I feel; dependant on trainer strategy.