Is this supposed to be a logic/behavior problem as people are suggesting? Are you trying to second guess the other entrants and chose the drawing fewest of them would have opted for the increasing you chances of winning?
-Eóin
That's up to you how you choose to analyze the question. I am just curious as to the reasons people would give for their choices, the thinking behind it. I asked this question to friends and family (offline) and the answers were rather interesting, so I wondered if the answers that DC members would give would be just as interesting.
Typical answer among friends & family
Based on the answers given by friends and family, I have come to the conclusion that most of them are in denial of their own greed. Typical answer was something like "I am not greedy, so I'll take the $250, because most people are greedy and will go for the $1000, giving me a better chance of winning the $250."
The way I see it, anything you do to increase your chances of winning is done out of greed. The only way your decision wouldn't be greed motivated is if you did something like toss a coin to determine which one to enter, or as parkint did and refuse to enter at all.