well i am getting Brenda J ready for my last trip (maybe). This year i would like to head south, just casual cruising without any schedule or destinations in mind. I am waiting until the end of the hurricane season, or rather until later in the season. The only part of the trip i am concerned about is the New Jersy coast, i will be alone and there are not that many places to lay up in a storm. I have a buyer for the boat when i get back so this could be my last trip. I urge people to go when they are young enough, at 72 i am losing my upper body strength,and am not sure how long i can safely sail. The main prep i have is bottom paint, the barrier coat held up, but the bottom paint is comming loose in spots,so i am in the process of removing it. A pressure washer is working to remove the paint --but it is slow. I did not contact my boat mover but would like to splash around Sept. 1. In prep the biggest problem i have is carrying too much. I enjoy working on things so tools and spare parts are carried to the extreme--will try to do better this time!!!!!!!!!!!!!
If you are planning SE coast around 'cane season, earlier is probably better than later. Most of the storms that cause issues along fl, ga, sc and nc are gennerally after labor day.
Not to say one shouldn't head this way then, though. It is pretty easy to work around storms...lots of warning and generally pretty good track predictions from nhc.
Good luck on the rest of your preps!