I give you a lot of credit for understanding the problem and trying to communicate it to an audience, but I’m not very sanguine about the chances of getting the value (or price) of pessimism across to optimists. ;) ;)
Me: “Oh alright. I’ll make one just to show you how your dumbass idea doesn’t work. THEN will you listen to me?”
How many times does Kirk tell Spock, “It’ll work, Spock!” ?
It only works because Spock makes it work after Kirk puts everyone’s lives in danger (or sacrifices some Redshirts).
The problem with trying to explain the subtleties is that few people understand how much was paid for that pessimism (relationships, broken bones, bank accounts). Optimism is cheap (and profitable in the Idiocracy). Competent pessimism is not. If one is a soldier, the grizzled old fighter might get romanticized in movies. For other occupations, it’s just the ‘improbable hick with a lucky hammer who hates people’ meme.