Sounds like a cool idea. Just hope the money doesn't drop else where. And if the homeless guy happens to be sleeping or on the side of the building(which is true in many cases), then dropping it would be difficult.
The drop will take place during a time with little to no wind in an area heavily populated with homeless. We also have a designated "hype man" who will be wandering the area ahead of time handing out breakfast bars and supplies while alerting the homeless of what will be taking place.