I think that modern roller furling gear is pretty reliable when correctly fitted even charters come back with it intact most times. I like Profurl classic myself. As I singlehand a lot of the time I would always have a roller reefing genoa with a foam insert. No it is not great but there is no way I want to go forward and wrestle with a 400 foot genoa 4 times on a typical sail from St Lucia to Martinique.
In fact I might get three Staysail, Genoa and a roller furling CODE ZERO!
If I was heading out to cross oceans then a windvane starts to make sense but for day sailing around the Caribbean an electric autopilot is what I would want. CPT make a wheel pilot with a good rep but almost any manufacturers below deck job will do providing the actuator is sized correctly. Why, well when I am raising or lowering sail I want the engine on and the autopilot maintaing the course I set not the one that the fluky wind round the lee of most islands dictates to a windvane. Also windvanes rarely do a good job in light wind conditions on wheel steered boats.