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Are you kidding me, /vp/? You're forgetting something really important in Pokémon.
Of course I'd love having someone like Cynthia, Karen or Shauntal by my side. But the true best travel partner is... Ash Ketchum!
Ash is the best partner. He is a magnet of disasters, conspiracies, legendary fights, hot girls in trouble, awakening of legends and other shit. With him by your side, you would be able to see the most awesome, weird and rare things in the world. Just imagine you being able to act like someone intelligent in all that situations he is always involved. This would be fun as fuck, you could get a lot of girls, rare pokémon, etc.
He's shit, but you could just treat him like trash and he wouldn't mind because he's fucking stupid (Remember Paul and Trip? That kid doesn't mind being bullied). You could just use him to attract fun stuff.