E- Boat Plan

Desert Island Boats

Ive been dipping into Lodestar Books republication of Francis B. Cookes Cruising Hints. Its an enormous and engrossing read and ideal when the weather is miserable and I cant get to the boat. When Ive got time to do it justice Ill review it properly.
In every page theres a line that will strike a chord with the single-handed sailor but one sentence felt so much a like a reflection of myself on paper that my wife had to ask why I was snorting into my tea:
"I... have searched in vain for the ideal small single-hander, but I think I have at last found her... She is a perfect love of a boat, and when my ship comes home, I shall be tempted to have her built. That is, of course, if I still remain in the same frame of mind; but yachtsmens fancies as regards to boats are as changeable as the seasons... The design I am in love with at the moment..."
...is actually not that far from a design that Im in love with at the moment.
Im looking for a camp-cruising open boat that I can build in clinker (assuming all goes will with the dinghy). It must be easily single-handed but have enough to keep crew entertained. It should be shoal-draft for the East Coast but be well ballasted so that my wife feels confortable when the wind picks up. It must go well to windward.
Thats quite a tall order.
Joel Whites slotted ballast keel on his 23 centreboard sloop gave me some ideas and then I ran into a similar solution on Paul Gartsides Half-Decked Racing Gaff Cutter #93.
I really like the plumb bow on the gaff cutter. A well lined-off clinker bow rising vertically from the water looks fantastic and makes the most of the waterline length. Im wondering if I can get a sail plan that would allow me to single-hand the boat with a small suit of self-tacking sails and then add others when conditions and crew allow.
If I can balance a club-footed jib staysl with the gaff or bermudan main for single-handing and then add a mizzen to balance a staysl jib when Ive got crew that would be ideal. In the picture the mizzen is ungainly and nothing is to scale. Im not a naval architect and dont plan to start dabbling - that way disaster lies.
This is probably far too much rig on a boat that will be less than 20 on deck but it doesnt matter - this is daydreaming. By next week Ill have talked myself into a Koster.