Two stories:
1) My pops worked in a major city for 38 years. Every few days, him and his friends would see a homeless guy on the same corner, so they would give him a few bucks. My pops later learned that the homeless guy owned like 8-10 buildings in Manhattan.

Guy was probably a millionaire. Did he just "get off" on pretending to be homeless? Some sick fantasy? Who knows.
2) Was in Manhattan and walked past a homeless kid about 21 years old. Stopped and talked to him. Apparently, he comes from a wealthy family, told me his dad is a surgeon and mom an executive for a Fortune 500 Company. I asked him why doesn't he just go home. Apparently, he moved out, wanting to prove to his parents that he could make it on his own. Started a business that failed and was homeless. He told me he doesn't want to go back home because of his "pride." He can't stand to look his "father in the face." Who knows how true it is. But, yeah, if it is, might as well just move back home and try to start over. Better than being homeless.