Re: How to Proceed...
The idea of the Thorny Path is not to fight against against the constant Trades and currents at a very slow, very uncomfortable rate. Rather it is to sit in a harbor until a frontal system comes through and use the short-lived favorable winds generated by the system to dash to the next harbor where you wait for the next favorable winds. At this time of year the frontal systems are way north so you might wait for a very long time. I think van Sant's approach is for the post-hurricane season, after November 1. Read the book to see how it works.
As for seasonality of hurricanes, we purposely crossed the Indian Ocean to get to South Africa before the cyclone (hurricane) frequency increased. We had to abandon Mauritius a lot sooner than we thought we would because a tropical storm was developing. TS frequency in the month was 3 in 10 years. It developed into a Category 3 storm (130 knots). There had never been a cyclone recorded in that month. Averages are just that, they don't tell you what is happening in any particular year and it was a waning La Niña year which should have made conditions even better.
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.