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Let's see...
I'm too lazy to roll, but not gonna pay CP to pick my region or age.
15 / Female / Kanto
Small town, -50
Shiny Gastly as starter with a mental bond, so -250
Free physical fitness with small town
Discounted Aura abilities, -300
I can't go without internet even in the Pokemon world, so laptop for -100
The other 300 I'd probably spend on general supplies. Maybe some Masterballs.
In the end, I'd choose to stay in the Pokemon world. Especially if that love interest that comes with the small town life is a cutie.