I've only ever reported homeless when they crossed the line.
I used to live near a creek in a city so homeless often line the banks and set up shelters in the trees against the back walls of the propertys along the creek. We had a gate so we had access to the creek if we wanted it (previous owner installed it). We had working relationships with the few guys that had built up against our wall. We left a hose running over the wall so they could have access to clean water. We asked them to be careful about leaving it running and we had a meter on the hose we could keep track of them using water. For years they were great. They would say hello if they saw in our backyard and they often thanked us for the water. If we ever had a party or anything we would make them plates or food.
Anyways for years all was well. Guys came and went. Some got jobs. Some just moved camps. But then someone started taking advantage of our kindness and they were using a lot of water (we suspect selling it to other homeless). Then they started hopping our back fence at night and trying to break into our shed. So finally we had to call the cops and get them moved.