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Pokemon is like Kirby. You have to make up your own set of rules in order to make the game more difficult. Here's how I'm playing Crystal
>Set
>Mom holds half my money
>no using Fly
>Cannot exit a Gym or dungeon to heal
>Can only use Pokecenters when I'm passing through a town or city on my way to my destination
>Only allowed to use healing items I find on the ground or get from NPCs, no buying potions and revives
>Must have at least one shitmon (thinking Aipom)