John - based on your and other concern, I think we agree with you about moving the boat. It will be somewhat difficult to stage out of Annapolis since it's a good 8 hour trip from our home, but I'd prefer safety over ease. My wife and I talked about it, and she's OK with me finding some crew and moving the boat. We could stage it in Annapolis and then head south to Deltaville.
I have two options. Option one has us going from Branford CT to Cape May, offshore around the east end of Long Island and then direct to Cape May. We would then go from Cape May to Delaware City, and then to Annapolis. Total hops - 3.
Option two has us going from Branford to Jersey City, Jersey City to Atlantic City (with a stop in Manasquan). Atlantic City to Delaware City (with a stop in Cape May), and then to Annapolis. Total hops - 4, with overnights in several spots.
I'd prefer option one, but we don't have a liferaft yet (on our list, but we won't be able to install it until Annapolis or Deltaville). I'm a bit concerned about going offshore without a liferaft, and I can't see renting one and keeping it in the cockpit. Also, what's the weather like on that route the first or second weekend of November?
Also, with regards to the bike, my wife did the Lake Placid Ironman this past July and she said she's OK with not bringing her bike, so we don't have to worry about it