I've only blacked out once since Gold, and it happened during...
the Bug-Catching competition.
My entire party was too overleveled to take part in the competition without OHKOing everything, so I pulled my Snorlax out of the box to participate. I believe it was a Pinsir that ended up getting a Critical Hit on me, and caused Snorlax to faint. Even worse, after the battle I "scrambled and lost $3200." I could understand losing $100 in the game, but I just imagined my character sticking his hand in his pocket and pulling out a wad of bills and tossing them on the ground before running away.