Several years ago I attended an event at Cross-Lines Community Outreach, one of our favorite service organizations in the Kansas City metro. People were divided up into groups sitting at tables. Each table was to imagine they were a single young woman with a small child at home, living on the edge of homelessness. You were presented with a choice to make. You rolled the dice to see what choice you had to make next. There were financial implications to all the decisions and a running total of your resources went up and down accordingly. The odds of things happening were based to some degree on actual experience. The game stops after several iterations and you see how many people were able to get out of poverty, hold their own, or for whom things got worse. It was a very useful tool.
Urban Ministires of Durham in Durham, North Carolina, has done something similar using a pretty slick website interface. Give it a shot and see how you do: