Hi, Scott:
Hope things come together for you this year.
Conventional wisdom and most experienced skippers like to wait til the end of hurricane season before leaving East Coast ports. This is/was (depending on who you talk to) around November 1. I've left in this timeframe and had a good trip via Bermuda from the Chesapeake.
The problem with waiting longer than this is the increased possibility of "northers", i.e., strong fronts which form to the north and affect waters as far south as the Caribbean. The "Christmas Winds" in the islands are an example. Usually, they only blow for a few days, but they can blow much longer, with winds up to 40-45 knots or so.
Delivery skippers make the trip at most any time of year, but they're daredevils
With the crazy hurricane seasons we've had extending longer into the fall (and apparently having trouble getting kick-started this year), a later departure might be desirable. But, I wouldn't want to wait too long. If it were me, December 1 would feel OK.
You might want to consult one of several "bibles" on passages south....there are a number of published references. Also, if you get a chance, discussing it with Herb (Southbound II) via email or phone might be a good thing to do, or one of the several weather routing services.
Bill