Re: Drilling a clean entrance & exit hole
You could use a hole saw. One with a good drill bit with length. Start on one side till about half way through, bit should exit BEFORE the hole saw blade, and start on the other side where the bit hole is. Perfect alignment and go back the other way, not pushing any frayed wood out.
A dremel with the Carbide cutting bit for Steel ($15 for one) does ETREMELY well on wood and fibreglass. Cuts like butter! I use it alot on my boat. Just some ideas?!:/