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I'd live in Unova considering I'm a New Yorker. I'd spend a good amount of time in Nimbasa City with my friends and the like. My main man would be a Raichu -- given to me as a Pichu egg in my childhood by my uncle, who used to travel loads till settling in, let's say Alola.
He'd have given me the egg to get me more active, to enjoy my childhood as it transitioned into adolescence. The Pichu hatching would be a surprise. A timid little thing that puts up a front of being scrappy -- faking it til he makes it. We wouldn't battle too much at first, but we'd bond spectacularly, taking trips around the region whenever we can afford to. It'd evolve during my early teen years. Having to commute using the subway more for trains would get me into battling. Pikachu, sneaky and crafty though he is, isn't enough to compete with multiple Mons in a team after a while, but that'd really spark something in us.
In come the others:
An Escavalier, traded to me by my best friend and probable rival as a Karrablast for a Shelmet, since he thought Shelmet was cooler.
And a Jellicent, caught while on a ferry as a Frillish.
They'd work together well, and evolving my Pikachu into a Raichu would be a unanimous decision as we try to dominate the Battle Subway. But that'd be an empty goal, and adulthood demands something more substantial. We'd see so many Pokemon via the Battle Subway that we'd want to travel beyond Unova, and making friends "overseas" via the internet and through other pals would be the perfect way to travel with a goal and destination in mind.
I'd work whatever jobs I could in any city or town I find myself in, seeing my friends and continuing my Pokemon journey.
A lot of my favorites like the Porygon line, Beldum line and what have you would join my team in rotations, and I'd probably do this for about two years before returning home, hopefully with a career path in mind.
That's the short version, anyway.
