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I think a lot of the problems come from people either not being educated on credit/finance, or just being to dumb to apply it. I'm 25 and have only worked full time the last 2 years since college, but I have 0 debt. No student loans, no credit cards, no car payment, not mortgage. That will change when I buy a house, but basically, if I can't pay for it, I don't buy it. When I had student loans (because really, who can pay for all of their education on their own?) and was actually earning money, almost all of it went to pay off my debt. I have credit cards, but only for convenience and because I get 1% back. I pay them off completely every month.
A friend in his 40s tells me I'm smart, because he built up $40k in credit card debt (now paid off.) I just understand that I'm not getting free money. When my car died, I bought a Corolla, because it made sense. I could probably have afforded the payments for a new Audi, which would have been nice, but then all my money would be going to pay someone else interest. Instead I payed cash from money I saved up. (not against getting car loans, just against outlandish spending.) I have a new flatscreen tv, but I've wanted one for years, and only bought when I could afford it.
In the D&D example, people want to run all the high level dungeons right away. If you don't level up enough beforehand you get crushed. I don't see how it's that hard to understand.
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