Thanks Jeff for that great write up. Very informative as always. While there is some truth to what saildog said about my write-up I would like to clarify some points.
Plastic ports - Thick Lexan of course is the window of choice but also the hardware that holds the ports in. Most production boats use very flimsy plastic to hold and secure the ports in place. In addition, those real big scenic windows, most would not hold up to a rough ocean and would blow out. This was demonstrated by a not so long ago Bermuda race where the boat sunk.
The chainplates in the newer production coastal cruisers have come a long way. But older boats, well we know what they are.
Cleats - I don't know one manufacture that makes a dedicated cleat for drogues and chute. Most cruisers use the stern or bow cleats for this. I have seen a big difference between a coastal cruiser boat vs a bluewater boat in cleat hardware and support. Look at a Malo cleat. In addition the stern design in thickness of fiberglass laminates where the cleats are is huge between the two. Not to mention all the dingy davits, Radar and solar power arches back there.
Rudders. I cannot comment on design except that as I read cruisers logs, rudder problems are abound for spade rudders. Either delimitation, or broken due to grounding or forces from the sea. But here I think quality of construction is to blame for most. The latest ARC had a few.
Water and Fuel. Well, 1 gal per person seems light to me. That is just for drinking. I believe most nutritionist will agree we should drink at least 64 oz of water a day. Put the heat of the tropics into play and the amount goes up. Than there is washing both personal self, dishes and maintenance chores on the boat as well. Quality of water supplies too becomes important in far away places. One can have a watermaker too on board and the compromise there is more fuel needs to be carried to offset the genset/engine that needs to be run to power it. One can live spartan if one chooses also. Fuel, my personal believe at least 500 miles min of fuel should be carried on boat plus fuel to charge the batteries. I cannot tell you how many cruisers logs tell of running out of fuel because of long periods of no wind or wind on the nose situations and are forced to motorsail. I don't like to carry large amounts of jerry cans on deck. I would carry a few just to get diesel and water to the boat where fuel docks are unavailable. I like I clean unobstructed deck. Personal choice.
While we all have are opinions and theory's of what a boat should have, I believe the best information is to read from cruiser logs and books on what really works and what doesn't. SSCA is a good start. We can what if until we be are blue in the face here but the people actually doing it are the experts. They are out there doing it, living it and dealing with the boat designs or the lack there of.
In closing most of the time it is not the boat but the seamanship of Capt and crew that makes things work. For even the best sometimes don't make it when mother nature raises up in anger.