Despite working as a fashion photographer, Mark Reay found himself homeless for 6 years living in NYC, a life event that's been documented in the documentary "Homme Less". Here, from the review by The Hollywood Reporter:

Reay, a handsome 52-year-old with the kind of hair that makes a man not mind the thought of graying, grooms himself in city-park restrooms and at the YMCA, where a few lockers contain his natty wardrobe and assorted possessions. A camera, cell phone and laptop make him a one-man photo crew, allowing him to shoot the backstage action at Fashion Week, edit and upload pix using coffee-shop wi-fi, and maintain as much of a digital presence as anyone else who works outside an office. He has health insurance and a bank account, thanks to his actors' guild, and friends — most of whom don't know he's been sleeping rough for five or six years. In fact, his current camp is on the roof above an unwitting friend's apartment, requiring him to move stealthily from sidewalk to rooftop lest he bump into the man in the stairwell.

Short footage from the documentary:

Reading about the film and having watched the trailer, I wondered how it came about, that Mark wasn't able to get him a place of his own. Film critic Mark Dujsik answers my question:

Reay pretty much admits he's homeless by choice, as a way to save on the expense of renting an apartment. After all, he needs the little money he earns in order to do the work he wants to do, which often includes networking at bars until 2 o'clock in the morning. He could get a "normal" job if he wanted, but he doesn't want to. Reay speaks directly to the camera, telling the audience that we can feel free to come up to that roof and tell him to get a regular job. "Kick my ass," as he puts it, and we can't tell if he means that literally or figuratively.

And the same does the following BBC segment:

Via kottke.org.