If there is a pumping heart and soul to the C-Dory clan it would be the two of you. Your generous website words not only contain much knowledge but overflow with wisdom, too.
The only folks I can compare you to is a couple of dedicated beach bums by the name of Ida Little and Michael Walsh. I remember whipping off a letter to them after reading their fine article "In Search of Anse Dufour: Canoe Cruising in the Caribbean" which appeared in Small Boat Journal in 1987. Their boating motto? Keep it simple, as in a canoe if possible. Ida graciously wrote me back a quick note about their new trailerable 36-foot liveaboard, built with an 18" draft so they could still ground out on sandy beaches in the Bahamas where they had decided to spend winters. (It was felt that a canoe was probably not the best craft for the trip over the Gulf Stream or as a long-term liveaboard.) The new boat's name? Beachcomber! At the time they were polishing off a manuscript that eventually came out as the 352 page "Beachcruising and Coastal Camping" (1992).
Beachcomber led them to more adventures which were published as "The Thin-Water Alternative" (Cruising World Oct 1998) and "License to Play" (Cruising World Sept 2001). The latter article summed up their philosophy best: "We chose cruising as a lifestyle many years ago, intentionally selecting a life in the wild with enough leisure time to appreciate it...For me, a day of bird-watching is a day well spent." Sound familiar?
I was thinking of following in their sandy foosteps, but my wife and I got sidetracked with a multi-year move to Australia -- a daughter then soon appeared etc etc -- and we never left our simple canoe and folding kayak modes. With the years rolling by, I'd like to get back to a long-term cruise by boat but a) don't like to abandon my old VW campervan (I hesitate in dumping it for a new tow vehicle since we only run one vehicle and will not get a second one) and b) feel guilty about going to the dark side and using a "stinkpot" on the water (a nice stinkpot, mind you, but a stinkpot nonetheless). Our VW land-based stinkpot gets about 24 mpg on the highway -- or about 6 times the cruising economy of a fuel efficient powerboat. Add a folding boat or canoe to the equation and there are thousands of places to explore. But, yes, it ain't the same and you can't get to a lot of out-of-the-way anchorages. And, yes, we're getting older and it ain't as easy on the back/joints/fill-in-the-blank. Plus we're cheapskates and the thought of dropping $50,000 to $80,000+ for a used boat/used tow vehicle in these recessionary times is a bit offputting. Keep it simple? Hmmmmmm.
We've driven from one end of the continent to the other using VWs and still manage to find some great spots regardless of the great unwashed masses. A couple of summers back, we had the rare privilege of watching 45 orcas go cruising by us no more than 20 to 30 feet away -- and we weren't on a boat but a beach! All of them zipped by to rub their bodies on that pebbly beach, with three of them sideways abreast underwater at the same time. A humpback was trumpeting offshore while all this was going on! Again, the cranky old VW got us there and we had a folding kayak to expand our watery reach. Not perfect, but it works. And at the danger of being considered a sentimental flake, that old VW is considered a part of our family, not a mere vehicle.
Would I do the Great Loop in a kayak or canoe? Nope. Which is why a C-Dory is a consideration. But is it the simplest cruising/travel mode, keeping K.I.S.S. firmly in mind? Hmmmmmm.
Decisions, decisions....