How weird. I've been on the streets, and standing in one post for hours on end, having to beg people for their pocket change, getting told off by some people, getting propositioned by men, and possibly getting arrested is not an easy or quick way of making money. I'm no longer on the streets, and I can tell you that holding down a job is far easier and financially rewarding than shaming yourself for a bunch of quarters and some dollar bills.
He must have something going on in his life to be panhandling, or perhaps he has some mental health issues or something, because I cannot, for the life of me, understand why anyone would want to pretend to be homeless all the time just because. Makes no sense.