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I'm not sure how well I'd be able to take care of six fully evolved Pokemon, so I think I'd rather stick with more mellow/gentle ones.
Can't go without Tangela. He's my boy!
I hate the water and can't swim, so having a handy Wailmer flotation device seems like a smart idea.
I'm also scared of heights, but Drampa is a kind and gentle dragon and would be attentive to make sure I'm safe while in flight.
Furret is adorable and cuddling up with one when things get cold sounds delightful.
Granbull is strong, but also a big softy. Perfect for someone that probably couldn't handle a Machoke or a Gurdurr.
Smeargle I think would be handy to have just for the utility of his paints, which could be used to mark trails to keep from getting lose or to splash in a dangerous Pokemon's eyes so we can skedaddle.