A lot of water could go into the cockpit with the transom open. It could drain out quickly too, but would pull the stern down pretty quickly. If you had concerns about getting pooped it would be pretty easy to install large drains through the transom.
Can't see in the photo but how much depth is there between the cockpit sole and the cabin opening? This is a vital concern because it is more important to keep water out of the cabinthan out of the cockpit.
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!