Reattach quarter-round molding under front door
Once you get the holes size gauged for the finish nails you will use, you will need to drill the holes once the shoe is in place to a depth of about 1". To help accomplish this, use a small piece of tape 1" from the end of the bit so when your tape touches the shoe, you know you are at the right depth. Your nails should slip into the holes you just drilled and when you drive them in, what has not been drilled will hold the nail securely. Drive the nail flush, or near flush, finish it off by setting the nail below the surface of the shoe with a nail set. They come in sizes, use the one that is the smallest, typically called 1/16"