I'm not a racer (though I have crewed - it's too stressful, I'll take cruising over racing every time) but the shots have been good and nice to look at. WRT the hurricane season, you do know that they can arrive early don't you? Don't wait too long to decide what you're going to do, find some good shelter. How much chain have you got? How many anchors? Don't leave it too late.
I am sure you will enjoy the beauty before the storms. By the way, the racing pictures were great. I am a bit envious but will be there next winter to enjoy the Caribbean. Have you considered heading north to avoid the hurricanes? It would be a change of pace, but it would be a different area to explore and experience. New York City is about 3 weeks north. New England and Maritime Canada are both interesting to visit. You could finish off in the Chesapeake region in October so that you would be set for a transit at the start of November. (My insurance won't let me head south of Norfolk until 1 Nov)
We got 3 anchors, it is OK for us to stay here for the insurance company if we follow the safety instructions and we could easily tie up to the mangrove trees here in Antigua in case a hurricane would arrive much earlier.
Yes we have in fact considered to sail towards the US. Maybe Miami for some months. We'll see. Have to apply for the VISA's first then we'll decide.