Down here in Cincinnati they usually do there business in "Band-Os" (referenced by Fetty Wap in "Trap Queen"), basically a boarded up vacant, abandoned house. McDonald's bathrooms are also popular destinations.
Only thing I seen similar was up in Manhattan. I exited the Port Authority terminal at midnight, and there was literally a homeless dude in a sleeping bag on every corner. Some were thoughtful in their positioning, others you had to step over. Don't think they were necessarily drug addicts, mainly older dudes who failed to achieve their dreams.
My last day in NYC I was waiting for the library to open up and this 60 y/o white dude in a Hawaiian shirt, khaki shorts and birkenstock sandals sits across from me, trying to sell me on a "caricature" (a cartoonish portrait). We start talking for a while, I tell him I'm tryna be a RnB singer, he tells me he studied at Hilliard and usually plays piano (busking) in the middle of the day as a side hustle. Despite being a senior citizen, he somehow knows who P Diddy an Jermain Dupri are and that they have offices blocks away. He then shows me some photos of some scantily clad white chicks he took, and it becomes clear to me he is a jack of all trades, master of none. a Backn the 1980s I assume he was probably running around on some kanYe type swag, telling everyone he was going to be the greatest artist of all time, and alienated all his family and friends.