Alice and Kev
I created two Sims, moved them in to a place made to look like an abandoned park, removed all of their remaining money, and then attempted to help them survive without taking any job promotions or easy cash routes.
The world of Alice and Kev is an experiment by Robin Burkinshaw, playing a homeless family in The Sims 3. It turns out that subtly subverting the given social norms of the game leads to a surprisingly poignant story. Wonderfully sad and funny, and well worth reading.