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>Starter
Either Krabby, Bulbasaur, or Croagunk.
I live just a few minutes walk from the ocean and spent a lot of my summers as a kid on boats and islands. Krabby would have been a great nautical buddy for those times. Plus he's got that aggressive nature like I do, so I feel like we'd get along and grow together.
As a three-stager, Bulbasaur could evolve as I grow. Bulbasaur to play with when I'm a kid, Ivysaur to adventure with now, and Venusaur when I eventually decide to settle down. I also love its calm, determined nature; Bulbasaur just seems like a great Pokemon to have by your side. Vine grappling things would be handy too.
Croagunk seems like a funny, cheery Pokemon who'd be great to hang out with. I can imagine getting a beer after a long day's work and chilling with my Toxicroak.
>Profession
I'd open either a restaurant or a Pokemon Gym. A restaurant because I like cooking and it's just a great way to make people happy. The Gym because I want to help people learn and I like government/politics, which Gym leaders seem tangentially involved in.