This is a great thread that I had missed, so glad that it was revived!
Was the picture below taken in Georgian Bay? Nothing says Canadian Shield country like the combination of precambrian granite gneiss and Pinus Strobus! I've never been to Georgian Bay, but that picture could have been taken anywhere in the Ontario "Cottage Country" lakes. It could even be here at my home in the Thousand Islands area of the St. Lawrence, an offshoot of the Shield known as the "Frontenac Axis".
Your "Drake" reminds me much of a similar shoal draft centerboard ketch that slowly fell to ruin on the hard in a marina in my home town of Alexandria Bay, NY. As a young man I used to love to look at the "Lotus" sadly fading away in a back corner of the lot. I would have loved to save her, but it was far beyond my capabilities at the time. I'm so glad that "Drake" has been lucky enough to find such a good caretaker in you...