Too many times we look for complex solutions when the answer is right in front of our eyes.
This is an old trick, but a good one – drilling pilot holes for nails using the nail itself. It works with both wire nails and cut nails.
With a pair of lineman’s pliers, clip the head off of one of the nails from the box you’re using. Make sure that it is good and straight, and that there are no protrusions around the area where the head was clipped.
Chuck this “headless” nail in your drilling tool of choice and use the nail itself to “drill” the hole. With wire nails, you can stop the hole when you get through the moulding. With cut nails, it’s best to make the pilot one-half to two-thirds the length of the nail.
This will result in perfectly sized nail holes every time. –Grant Burger