I've been 10 miles offshore in the N20, it was light air and the sea state was mild. I would be concerned about doing a Cuba run without adequate preparation and preferably a few chase boats. Would I still do it without chase boats? Probably because I'm crazy and I've also had some major gear failure offshore before that we've managed to work around in areas where there is no beach support.
As far as an F16 mast not being capable of sustained reaching loads, this is the first I've heard and its concerning. Karl, is your plan to switch to an F18 section cut down to the appropriate height? Why would the carbon not be better? Carbon is usually stiffer and capable of sustaining higher loads for the same weight as aluminum. Would Falcon would build a tougher Carbon mast for you if you asked?