First thoughts:
I really like the setting map.
So to clarify my understanding, you play a pokemon and their trainer? Can you trade away one of the roles temporarily to make scenes easier with your pokemon?
I like the Fire playbook quite a bit. 2 suggestions on it:
Feud with a friend might be better expanded to something like start/act on a feud with a friend. Maybe. Something that makes it a little smaller. I'm imagining feud as a long term fight and that might be a misunderstanding.
Go over your depth might be better rewritten as "get in over your head" or "get stuck in something you can't handle"
I like how you're implementing duo and shared moves.
I really like the other roles as well. Lots of neat moves.
Do the pokemon and trainer share tokens?
I also like the setting elements. I think there is a lot of potential there. I wonder if the constant battles element should be darker to highlight more of why we left but that may not be necessary.
This is really an excellent draft in my opinion.