tho this descended into semantics about the nature of luck and chance in the game, it should be noted that Chibi must have meant 'good luck' in a conversational manner and not literally, 'I hope that you are good with rainbows and leprechauns as this game has aspects that hinge on the roll of the dice' however, I think it's good to analyze games and see whether it takes more elements of chance, like Sorry, or a balance, like Parcheesi, or straight up strategy like Chess.
I think that whatever pattern Simon gives you comes down to chance as well, some were easier to repeat than others, but that was an optional puzzle, not necessary for game completion.