Hey Listen!
Nathan :D
I would just pursue the adventure of the protagonist. I have dreams about this stuff. I feel sadness when I wake up and can't go hang out with lucario 

I'll throw in a little bit of things.
With the story in the pokemon games, they're a little unbelievable. Don't get me on the whole "the story is unbelievable yet you can believe pokemon" nonsense. Go with this.
A kid going out on a journey, for the first time ever, isn't going to have a crazy adventure like that. It might get pretty intense at times, but it's going to be a lot more slow paced.
Eventually you might have this awesome adventure, but that's going to take years, walking over your entire region.
Anyway..
If I had a job, I'd probably go into the science of things. I'd like to go out and study the pokemon in their habitats, study their hunting and natural behavior out in the wild. I would probably get into training pokemon as well, since I would need a way to protect myself. After a few years of study I would probably get into doing the gym challenges and maybe eventually the league.
Alright, new question.
If you could have any job, or if you're a trainer, what sort of trainer would you be?
In the anime, it's canon that the starters live in the wild though.
Realistically then, I'd probably end up as a small town pokemon breeder or someone who makes medicines for pokemon. My pokemon would probably end up being the common pokemon like Rattata and Pidgey, or common bug types since the area around here is mainly fields and forests.
That or a purrloin I was gifted for Christmas.
That's anime canon, though.
The main games and the anime don't share canon. =/
but yeah, that's what I'm getting at as well. The starters are gonna have to live in the wild somewhere, but nobody knows where really.
But if you evolve your Pidgey to a Pidgeot you could have it fly you to other places. I think you could fit on a Pidgeot.. I think they're like almost five feet tall and around 100lbs, give or take.
Depending on where you live you could be close to another town, or even a city that has methods of transportation that you could take advantage of to go off to other places.
How would you guys feel if there were a game that looked sort of like this hack but more 3D rendered. Personally, I would love it. I like overhead views better.