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.
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!