Guest,
Drill and fill is expensive as it takes a lot of labor and a kiln dried sand that can run up to 3 times the cost of regular top dressing sand. Here's my take on drill and fill. If you have non-permeable layers that the drill will penetrate, then this method has merit. If, however, you have pushed up greens with a fairly uniform soil texture, then all you're doing is punching deep holes and filling with sand, but you are not improving drainage. Think of a 6 inch piece of concrete. Drill an 8 inch hole and you create a channel to the soil under the concrete which may drain better then concrete. Now, if that concrete is 2 feet thick and you drill a 18 inch hole in it, have you improved drainage? Short term maybe, but not for long. If you are trying to improve drainage, drill and fill may work if you are penetrating to a faster draining soil. If not, other methods can be used to move water through the green.