Sounds like a nice opportunity.
As for rounding Hatteras, my guess is it all depends on your fortune with the weather and you just need to listen to the forecasts and make prudent decisions based on the crew comfort. The suggestions above are good to know in case the weather does turn nasty. Last year when we delivered Wandering Star from FL to LI the very best sailing we had on the 14 day trip was the day we rounded Cape Hatteras. Had we been there 2-3 days earlier it would have been a real whooping, and the next couple days after along the DE and NJ coasts we had very thick fog with little to no wind. However, we hit a nice window leaving Charleston and had nice smooth sailing all the way around the outer banks. The only real challenge we faced in that area was the next morning off the coast of VA when the USN was conducting live firing practice in the area and broadcasting incorrect coordinates for their firing range.
Good luck with the trip. Please write a report about the experience when you're done.
Pacific Seacraft Crealock 31