Sky Claw gets a Charmander. Take Glowfire (you can find the restrictions last page, it's the one Burke rejected).
Note: I'm not that familiar with gen 1, so just take out any restrictions that don't apply/are impossible in that gen. For Pokemon colours, go use a pokedex fromGen IV and onwards, and since health can't be red or yellow or green, then just make it that she can't faint Green and Yellow Pokemon, while she must attack at least once and damage any black and purple Pokemon, but not kill them. That should make it possible to do in Gen I.
Anything else I've missed, take it out if you can't do possibly do it in Blue.
Edit: your Charmander, named Glowfire, has to be female. It just has to be. Soft reset until you get a female Charmander. Yes, this challenge is designed to screw with you, to make you repeat motonous tasks or calculate the unquantifiable. And punish you if you fail.
That's why Glowfire also has an item restriction. Every battle, she must hold an item. If she doesn't, don't use her. Next, she may hold any item, but to switch items, you must throw out 5items from our bag, any items, be they poke balls or star pieces or whatever. They must cost at least P7500 in total, though, if bought from a Pokemart.
Next, search your pokedex for all the Pokemon which are either black or purple. Any time you see one of these, Glowfire must land an attack on them, or however many attacks it takes, to leave the opponent in red health. However, she must not kill them, only leave them in red. If she does kill them, then you must retire her until you reach the next gym (so if you screw up after Viridian, then you're left without a Charmander until you get out of Victory Road at the Elite 4).
If, however, you see a Pokemon that's green or yellow (again, by the pokedex if it's not glaringly obvious), Glowfire cannot attack the Pokemon with anything that would leave it in the red nor kill it. She can harm it, as long as it doesn't go into red health as a direct result of her attack. If she does leave it in red health, or worse, kills it, then you cannot use her during the next five trainer battles.
To make sure this really screws with you, if you don't send her out into battle, she can't use Fly to take you to other places, and this resets every time you sleep/turn off the DS. So each time you play, you have to battle using her or else you can walk all the way to the next city. Oh, and she must lead your party every battle, not including the battles you have to solo.
Edit 2: when you beat Viridian Gym, then Glowfire may choose not to lead your party, but must still fight in every battle, aside from those against green and yellow Pokemon.
Edit 3: make sure she's holding an item, if she's not she mustn't battle, and this overrides all other restrictions. The upside is you can avoid the nasty restrictions. The downside is she won't gain any experience, and the day care is off limits. So plan your journey wisely. I should also clarify removing her item takes P7500, and then giving her an item costs another P7500, however if you just switch items (immediately) then it'll only cost you P7500; you won't be charged twice if you swap items.
