Napa Valley, California
Granted it's cold up there, but if eating is important to you, it's the easiest place in America to kill a cheap meal. One moose and you're eating well for a year (click here for moose recipes). The frigid temperatures ensure you never have to worry about refrigeration. And rumor has it, anyone can move into the mayor's mansion.
Lots of solvent people flock to the beautiful Napa Valley. But so far, it's a well kept secret among indigents in the know. The weather is temperate enough to sleep outdoors year round. The pace, leisurely. Hotsprings and fountains abound for bathing and laundry. Some of the country's finest restaurants have dumpsters here, not to mention the culinary institute. And as long as you're mildly presentable, the constant wine tastings ensure you'll always be up to date on the latest crop of Merlots.
Beverly Hills, California
Great weather with the nation's highest quality garbage can content per capita. It's also one of the few places in the world where no matter who you are, some reality show director could discover you and make you rich and famous beyond your wildest dreams. And you might even get a free facelift out of the deal.
If you can overlook the weather and would gladly give up any chance of employment in order to have a roof over your head, then Detroit just might be the place for you. Detroit has over 12,000 abandoned homes, and factories just waiting for someone with a loving touch to squat in them.
Anywhere in Mexico
It's got great weather and a low cost of living. Almost any pharmaceutical drug you need is available cheap and without a prescription. You might even be able to pick up some work gardening and keeping house for your ex-cleaning lady, Carmen who moved back to Mexico and bought a house after she made a small fortune working for you in the 90's.