As for all the concern about the weather, the trip from the Canaries to St. Lucia at the end of Nov, beginning of Dec is pretty much a milk run, except for the occaisional squall and they are few and far between. Last year my friends had to jibe once after they started heading west, so I really don't think anyone will be "working their backsides off". Of the dozens of people I have talked to that actually made this trip it was one of the greatest experiences of their lives.
They are not going from Canary, but from Azores, that are 750 nautical miles to the North.
There is a famous Transat race that at the first and second weeks of November passes near Azores. Almost in every edition they experiment strong winds and many times big storms when they pass in that area. On the 2002 edition 3 60ft racing cats capsized there and they had already their sails down. I know that a cruising cat is not a racing cat, but come on, a 36 ft cat on winds over 70K and huge seas? Would you risk a fair possibility of encountering those conditions?