http://www.city-data.com/ is pretty good for this sort of information. The forums are very active so feel free to ask subjective questions that are particular for your situation.
Author Lee Child has written a series of fictional novels which feature Jack Reacher, a former Major in the United States Army Military Police Corps.
Since leaving the Army, Reacher has been a drifter. He wanders throughout the U.S. because he was accustomed to being told where to go, when to go and what to do for every day of his life from military childhood to military adulthood. He also felt he never got to know his own country, having spent much of his youth living overseas on military bases and at West Point. He usually travels by hitchhiking or bus. As a drifter, the only possessions he carries are money, a foldable toothbrush and, after 9/11, an expired passport and an ATM debit card.
He wears his clothing for 2–3 days before discarding it, usually purchasing new clothing cheaply from chain outlets. He has no steady income and lives on savings in his bank account and part-time jobs. Since he has no fixed address, Reacher often eats in diners and other inexpensive restaurants.
Except that they're fictional and any time he runs into a bind something falls out of the plot hole to save him. It's not a very good way to reflect on how someone would deal with that situation in real life.
And, even without plot holes, a lot of the strategies that he uses work for him because he's a huge guy, with years of hard experiences in the military police. For example, he may have problems getting people to pick him up when he hitch-hikes, but he rarely needs to worry about his own safety with whoever gives him a ride.
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http://sfbws.com/activities/2013/07/06/drawbridge-van-excurs...