A guy my dad knew back in the 80s had an interesting scheme that he once told me about. During the warmer months, he'd live on the streets asking for money, sometimes making up to $100 a day or so. He'd of course blow it on booze or drugs, but occasionally would eat a "nice" dinner. As the weather got colder, he'd either break into a business and wait for the cops to show up or do some other petty crime so he'd be arrested and spend the colder months in jail. He'd be let out the following spring and repeat the process. He did this for 3 years or so until they finally caught on to his plan. He was an intelligent man, and had previously worked a factory job, but decided to live the vagrant life. He did a few years later of a heroin overdose.