Seems like he gave up on taking care of himself—living with sister or kids for years. Should have changed his career too. Freelance writing doesn’t pay well to begin with. He could get a menial job and make more than what he probably earned. Also, if I were desperate, I wouldn’t live in the city where expenses are through the roof.
There are organizations that would give him a free bus ticket to Florida or Houston, room and board, a cardboard sign and daily rides to an from his assigned intersection.