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>Grotle
There were quite a few different kinds of turtles living around my house when I was younger, so a Turtwig would be a reasonable option for a starter. Probably be holding off on fully evolving though, Torterra are big.
>Poliwhirl
Directly across the road from my house, there's a reservoir on a hill. At the end of the road, there's a river. In the woods behind me, there's a little creek. Unsurprisingly, we have a lot of frogs.
>Magnemite
That reservoir I mentioned? Feeds into a small electric plant by the river right around the corner. There would probably be a few of these floating around.
>Duskull
Just down the road and visible from my house is a pet cemetery. We're the closest house to it, so ghosts looking for someone to haunt might end up visiting.
>Braviary
It's not that common, but we do have bald eagles living around my house. Having something that can fly me around is cool and amazingly useful, so I'd go out of my way to catch one of these.
>Ursaring
I've always known there were bears around, but just last year I woke up to one outside my window pulling down a bird feeder.
Caught in that order, most likely. Food and care might start to get a bit expensive towards the end, but I don't think it'd be too unreasonable. I'd save on gas money with Braviary around, at least.