Hey Matt, you're the expert, man, but I don't quite understand what you said - with holes cut out for ports I was able to apply more layers of glass, and or epoxy or whatever and clamp everthing down tight from the top and inside the hull. Including strengthening the stanchions and repairing stress fracture leaks. My OLD 16 is still sailing and the deck is rock hard. It isn't easy working through a five inch hole, but if you glass before you add the trim ring you have a little more space and less chance of gumminig up the threads.
Besides, without ports how can you carry a fat cat bag full of beverages?