shiny_magikarp
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And if Winona's Gym is a Sky Battle?
That would be neat, but it would force you to either over train one Flying type, or train a bunch of Flying types.
I can see them giving you a Flying-type or Levitating Pokémon around that point in the game so that you have some options, similar to what they did with Lucario and the Lucarionite in X/Y. Maybe a Lunatone or Solrock with a nice Rock-type move (lol) to make the battle easier.
Though the fact that you would be forced to use a Sky Battle-eligible Pokémon for a battle--a Gym Leader battle, no less--means I doubt Winona as a Gym Leader would do Sky Battle. Maybe outside of the Gym, sure.
Perhaps battle for Mega Ring with Winona would be a Sky Battle.