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I have a mega-autistic headcannon about the world's history that I posted on a similar thread a few months ago.
>Regions = countries (or sovereign states). While the games sometimes contradict this (like with the name of the National Pokédex), I think it makes sense. I don't think that the Pokémon World is just a 1:1 copy of our world with Pokémon, so all regions have more or less the same size, so Kanto is about the same size of northern France (and not real-life Kanto).
>The small towns and cities of the games are just abstractions. The anime paints a more accurate depiction of how they are.
>Highways, railways, etc. connecting cities do exist, the reason they're not in the games is because it's tradition for trainers to "take the long road". Also, you're a kid/teenager and can't drive.
>The Pokémon League isn't the same thing as the region's goverment. They might or not be a part of it, but they aren't the same.
>Pokémon are used in warfare, though their use is not general and widespread as the upkeep of a Pokémon is very costly and training one is very difficult.