It’s not a running joke, but I loved when Craig called out Pete for not realizing he is wealthy.
Pete’s answer to many things is to throw money at it (most apparent in his DVC show where his advice is “just buy more points”).
One episode of the Disney World show Craig inadvertently called Pete on it, tried to backtrack, and then tactfully made his point. It went something like.... ‘I can’t afford that. You’ve worked hard and deserve what you have. I hope to be there myself one day, but not everyone can afford to do that.’
It was funny, true, a little awkward, and I wondered it we’d see Craig again. LOL