An extremely interesting theme! I'm not totally sure if I get your interpretation of redesigning failure, but the P̶o̶k̶e̶m̶o̶n̶mon theme is really fun!
At least the intention is for all the rolls to represent the Trainers' child-like innocence. Sometimes, failing that roll, not being innocent enough, can give you benefits, like being able to push your Mons to harder training or use the shady businesses, at the cost of your innocence.
