Yep, it is eating at you little by little. It is a great opportunity to get some real sea miles under you on a boat that you are dying to see what it is really like in real conditions. To have a skipper that has that much experience to mentor you is also heavy sand.
On the other hand....there are hurricanes until late October and no one can predict track or occurrence this far in advance. So, it comes down to a calculated risk, doesn't it?
Remember last year the French boys delivering a large factory Cat flipped it somewhere off the east coast
of USA? Shizzle can happen anywhere and at anytime of the year. Personally, I would accept the risk and take the offer. But I am a risk taker by nature...
The main thing is this...make a decision and don't look back. Do it or don't do it...stop beating yourself up with indecision. That is not an endorsement to go ...nor is it a judgment of weakness or strength if you stay home. It really is about calculating risk versus rewards. That is why I would go...for that reason alone.