What's wrong with just drawing? I'm a lazy bastard that can't help but play video games instead of drawing :[ . No one but me can procrastinate without even wanting to do so! Also, if I just draw, I know I'd just start from Bulbasaur and go all the way up in national number order.
An Idea I have is to have short goals that will vary depending on pokemons. Something like participating in Pokemon contests/musicals for certain pokemons, beating certain badges, beat all the trainers in the Sport places. I'd need many goal however, in order to have at least one that fits every pokemon.
EDIT: Think I have an idea. What I could do is cheat to get myself two of a selected pokemon (with only one Move Tutor/Egg Move), a bunch of Rare Candies, and a code to reset Gym Leaders, so that I can fight them as much as I want to and not include the hassle of training them between Gyms. I'd need a way to select pokemons thought.
RE-EDIT: Alright. I got myself settled over a particuliar set of rules.
-The goal of the challenge is kind of a Speed Run using a particular pokemon. The Challenge starts right after I defeat N the first time (With his lame Purloin that crit'd me to death) and ends as soon as the 8th badge has been obtained. I try avoiding as much battle as possible, to make it faster.
-I use only 2 pokemon of the same Specie, at the first evolution. Both are of different genders. Variations may apply if it seems fit (such as Latias/Latios, or a Female Vespiqueen and 3 Combees).
-I draw a Gijinka picture of a pokemon the Gym after I have gotten the pokemon.
-The Pokemon chosen goes in Alphabetical order. That means the first is Abomasnow and Snover.
List of stuff to make it easier:
-A huge stack of Rare Candies, PP Ups and Max Repels. I cannot use a Rare Candy to make my pokemons over 5 levels higher than the Average Trainer. Also, all TMs already hacked in.
-A hacked pokemon, which has many HMs and SoftBoiled. His stats are 800 HP, but 1 of everything else.
-I may manually evolve a pokemon that requires Trading 10 levels after it evolved. If it does not evolve before, then I may make it evolve at level 25.
Rules of Pokemons:
-A Pokemon may start with 31 IVs everywhere and 510 EVs already set, in order to head toward a particular strategy.
-A Pokemon may start with only 1 Egg/Move Tutor/Event Move. It's power may not be over 60.
-After beating the 3rd and 6th Gyms, I may teach my pokemon a TM/Move Tutor/Event Move. It may not have over 80 power for the 3rd Gym.
-It may have any item equipped.