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.
In South Africa doing lots of boat stuff. Departure north from Cape Town around December 15th. Arrival in the Caribbean around the beginning of February, after 5300 miles or so.