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>How hard would it be to catch Route 1 mons? Cave, water, forest encounters? Pseudos assuming you can find them?
(assuming you mean in general and not based off of Pokémon that'd live where I live or something) Route 1 would be piss easy. Literally just set out some food for a Rattata or some shit and bam, you have your mon. Rock types in caves would probably also be about as easy as picking them up and not harming them (the bats would be way harder for obvious reasons), Pseudos would probably bite your hand off before you could even try, etc. The games give a pretty good estimation of how easy it is to catch any given thing with catch rates; pretty sure they're not meant to be literal representations of how good the ball is, but instead catch-alls to signify the difficulty level of what you're attempting to catch.
>Would (you) find a Pokémon useful in your current job?
I'm still studying but trying to get something at minimum wage to support myself. I think a Pokémon would be more useful for studying than any job I could get at the moment. Then again, just having *someone* there for me would help, so maybe that doesn't count...
>Do all Pokémon speak the same language? To what extent can they communicate with humans?
I go along with pic rel as a headcanon because I think it makes sense considering Mew and it keeps a bit of mystique around the Pokémon instead of just making them "literally animals with superpowers".
>How do trainer battles handle the concept of the victor being awarded cash? How does it affect the economy?
It's probably just common courtesy. I like to think it started as a dare amongst kids and just stuck around when those kids grew up. It's probably not set in stone as a law or anything.
>Any region you'd settle down in? Which town?
Hoenn, probably in Lilycove. The Safari Zone is fun, the city looks gorgeous, contests are right there if you want them. I think it's just situated and built very nicely in an already-nice region.