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.
Back to Grenada in early December. Not sure I will remember how to sail. Will spend the winter and early spring in the Caribbean and then head to Bermuda and the northeast US. Still trying to decide if we will bring the boat to Canada, either in 2015 or 2016.