Our newspaper guy shakes us down twice a year. Summer and Christmas. We only pay him at Christmas and after two years I think he's figured it out as our paper hasn't ended up in strange locations. I do feel uncomfortable taping it to the box, but he seems to get it.
He is good, paper in a puddle only once. He double bags if it's raining and sticks it in the box instead of on our driveway. But still, twice a year?