A neighbor of mine enters every sweepstakes she can find, sending in dozens of applications per day. She wins at least one prize a month, ranging from kitchen gadgets to trips. The listed likelihood of winning is often an underestimate, she says, since some sweepstakes do not receive the number of expected applications. This is a life-defining hobby for her: it takes a significant amount of her time each day to find and enter these contests; most of her stories center around the prizes she's won. Here is an article about a woman in a similar situation: http://www.post-gazette.com/pg/08335/931083-54.stm