Re: Best used cheap blue water boats 30-45ft
I think you should consider displacement and sail (and anchor) handling systems when considering boats to singlehand. For example, a Westsail 32 is almost 20,000 lbs while a CS36T, just for example, is closer to 15,000. The CS, and lots of similar boats, has a lot more space and is much faster. It is also a lot easier to handle under power getting into and out of docks. It is also a pretty rugged boat. BTW, not saying you should buy a CS, just that there are other directions to look.
As for systems, when it comes to things like winches and wind lasses, many boats have marginal ones since it was a good way for the builders to save money.
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!