Currently, the rules for all cups state nothing about doing the cups in order, from crappy random stages that nobody wants to play cup, to clogan cup, to waluigi cup, then finally very special cup. Is it allowed to go out of that order, or should the rules be updated?

i'd say run them in order, but I get that it can be frustrating when you're 20 minutes in and you get f*cked by the game at the very special cup. Leaving it up to the player would be my suggestion but they'd have to note their order in the description for their run