I'm based in Florida and from what I've seen around here, many of the people who are spending money like this truly can't afford it. They have no savings whatsoever. There are multiple threads on Disboards.com about selling your plasma to take your family to Disney.
It's amazing what people do out of pride/vanity these days. Disney's $6,000 for two nights hotel & Disney's $5,000 cocktail are outgrowths of this.