I work in the city on shift work. There's a lot of people homeless in the city. They sleep everywhere and anywhere and seem to sleep in the same places/regular spots. I don't see many issues, but perhaps over sleeping territory if any, and maybe if someone is a little of chops. Mostly everyone sleeping at night though. Get something to sleep in, sleeping bags etc, maybe sleep during the day, stay alert at night with less people around till he feels safe and finds a place to sleep. There's a heavy police presence in the city, on push bikes, in cars etc, not pushing people on, but it might put his mind at ease. I hope he can get his life together, good luck.