Broken systems always seem to pop up, as do ways of exploiting them to make money. Steal This Book describes all-expenses-paid vacations to gambling resorts th

Broken systems always seem to pop up, as do ways of exploiting them to make money. Steal This Book describes all-expenses-paid vacations to gambling resorts that existed in the U.S. in the 60s and 70s. The condition was you had to buy hundreds of dollars worth of chips to gamble with. They were specially marked such that people could gamble with them but not cash out. People realized you could just play red and black against each other in roulette to exchange those chips for a complete set of regular chips that could be cashed out. (They would usually make many small bets and incur the small 0 and/or 00 cost once or twice rather than one big bet and risk losing all the money.) Practically free vacation.