JHomer,
I encourage you to get started on a guideboat. Yes it will be a challenge, but a very satisfying one. There are a lot of amateurs, including myself, who have been successful in building guidboats. I recommend that you read Kenneth Durant's "Adirondack Guide-Boat" and Dr. Gordon Fisher's "Tale of an Historic Adirondack Guideboat and How to Build One".
I usually lay out my plank lines on the ribs after the ribs are fastened to the bottom board. The shape of the lines is based on the sheer line and the width of the planks is determined by the number of planks used, usually 7 or 8. One could make a full set of plank patterns based on the lines laid out on the ribs. More often, after a completed plank is hung, stock for the next plank is clamped in place and the mating edge is scribed onto the stock. This is one of the trickier processes in guideboat construction.
Yes, each tack hole must be drilled. The size of the drill is based on the size of the tack which is based on the thickness of the planking. I think I'm using a #60 drill for #2 tacks in 3/16 planking.