Taking a look at the review thread for the Elesa episode, I think Ash is getting his groove back. And I really wasn't complaining that Ash lost. That actually was part of the plot of my abridged episode story thing.
As for for the last one, I think you confused this show with another high quality production.
Anyway, I never answered it myself...
How I would do it: Ash would bring out one of his big scary Pokémon (Sceptile, in Kanto Battle Frontier) and hold May's hand as they walked through the dark together. Maybe May kisses his cheek when it's entirely dark and he can't see.
How it would actually happen: Ash would call up a non-canon friend on a non-canon device in order to get May to believe the full moon would be bright enough for them to see under.