Using a 2x4 is a pilot is a brilliant idea. I will definately do that.My main concern is that if I drill from the outside in, I might come in a bit high, or low, in relation to the deck. On the other hand.....if I go from the inside out, I wont be able to get a good 90 degree exit in relation to the deck, as the drill itself won't allow me to get to that angle......resulting in a slight downturn. I think I may be over-complicating things.