Seems like you have some pretty dissimilar boats in your list. The Sabre, Tartan and Bristol are quite alike conceptually and different from the others. Perhaps a first step would be to zero in on your particular trade-off of quickness vs displacement. Each of these has obvious advantages and disadvantages and you have to decide what you want to do with the boat now and in the foreseeable future.
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!