Your plan seems pretty risky to me. The Thorny Path is quite slow since you have to wait for the appropriate weather systems before heading to the next anchorage. These systems are much more common in the winter when the whole meteorological world shifts south. With what the jet stream is doing now, I would imagine the Trades are very well established and likely honking. Trust me, going hundreds of miles to windward in strong Trades is something to be avoided.
If a hurricane/tropical storm is coming I don't think you could get to South America ahead of it. Once you knew it was a threat to PR
you would only have a couple of days (say 250 miles, don't know fast your boat is) and SA is a long way away, especially if the storm turned left a bit.
If I were you I would be looking for a November departure for the Caribbean. Find a really good hurricane hole or marina in Florida and spend the time sailing your boat and fixing the problems that emerge. Will a really clear forecast, ie no sign of a tropical disturbance even off the coast of Africa, you might head into the Bahamas but not too far. Be ready to head back to your bolt hole at the first sign of trouble even if it is 1000 miles away - think in terms of days both for the storm and for your retreat. You don't want to lose your boat, not to mention your life, in the first few months. Read van Sant and Cornell and trust their advice.
Wasn't St Croix Danish at one point? Wonder if anyone still speaks Danish? BTW, if you want to work on your Spanish I believe that some folks in Florida speak that language.