Someone did this experiment and wrote a book about it:

Scratch Beginnings: Me, $25, and the Search for the American Dream

http://www.amazon.com/Scratch-Beginnings-Search-American-Dre...

I had the same problem with "Nickel and Dimed" that I had with this game. She made a series of completely irrational decisions which resulted in expenses larger than they needed to be.

As a counter to this, I highly recommend Scratch Beginnings by Adam Shepard. http://www.amazon.com/gp/product/0061714275/ref=as_li_ss_tl?...

The summary, from Amazon:

Adam Shepard graduated from college feeling disillusioned by the apathy around him and was then incensed after reading Barbara Ehrenreich's famous work Nickel and Dimed—a book that gave him a feeling of hopelessness about the working class in America. He set out to disprove Ehrenreich's theory—the notion that those who start at the bottom stay at the bottom—by making something out of nothing to achieve the American Dream.

Shepard's plan was simple. With a sleeping bag, the clothes on his back, and $25 in cash, and restricted from using his contacts or college education, he headed out for Charleston, South Carolina, a randomly selected city with one objective: to work his way out of homelessness and into a life that would give him the opportunity for success. His goal was to have, after one year, $2,500, a working automobile, and a furnished apartment.