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Starting in Alola seems like the best deal, somewhere like Seafolk Village probably, or Malie City.
Ideally having a Gible would be great since it's my earliest bro, but it's a pseudo and its evo is Cynthia's partner so my autism prevents me from choosing it.
I'd also like Mienfoo, but since I'm not athletic it'd grow bored with me.
So perhaps a Gligar then. I'd evolve it as soon as possible, train until we can wreck shit, then get a place in Alola's E4 and replace Kahili for monotype Flying because she's incompetent