Re: Singlehanding a 41' Hunter DS?
A sixty footer would require a couple who really know what they are doing or even having full-time paid crew. If you could not be comfortable living on something around 40 feet or even smaller perhaps the condo route is best. Also check out a catamaran as someone suggested. By sailboat standards you get an immense amount of room and twin engines makes handling easier but there is still a big learning curve. Also with a cat if you are at the helm you are a long way from the dock when it comes to getting lines ashore.
Final thought, the 'big bedroom' style of boat tends not to as good if you want to sail long distances as something like the HR. You might also check out new Amels. They are gorgeous boats with lots of space and a ketch rig makes sail handling easier. Expensive though.
Heading back to Lake Ontario for this summer. Relatively few stops along the way from Grenada. Martinique, Guadeloupe, St. Martin (must have something to do with the French food), then Bermuda, New England and up the Hudson/Erie Canal. We were going to go via Newfoundland and Labrador but June remembered that one of the kids is getting married this summer - details, details!