Re: series drogue or para anchor?
I have a parachute sea anchor but wish I had series drogues since you are much more likely to be in the conditions where you might use them (say 40 to 50 knots). The parachute system seems more helpful in conditions above 50 knots sustained which you are highly unlikely to get on your trip.
Do you have an inner stay on your boat that you can use for a small staysail or storm jib? Also backup for your self-steering makes a great deal of sense. Hand steering for days with a small crew really sucks. Don't ask how I know.
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!