Here’s a story about a guy who won Cash for Life in a lottery in Michigan back in 1990’s. $1000 a month for as long as he lives. Problem is … he went bankrupt. His creditors are now auctioning off the lottery winnings, but you can only collect as long as the original winner is still alive. He’s 72, and the creditors will not disclose anything about his health, Bidding starts at $30,000. Question is: would you consider this a worthwhile investment? You’d make your money back in 3 years if the guys stays alive, but what if he doesn’t?