Re: Heading South - departure time?
Sounds about right to me. Many sailors seem to time their trip south with the Annapolis show, which is Oct 4th to the 8th this year.
Of course, it's also hurricane season, so weather will dictate timing.
The NJ coast seems to often frustrate snowbirds. If you can get a benign window (about 24 hours) with something other than the prevailing SW winds it would make the trip a little easier.
Otherwise you're beating into the prevailing winds.
Once inside, barring any serious weather you can usually make continous progress south.
From Cape May, you have the option of staying inside ( Delaware bay to Chesapeake) or remaining offshore, with the option of coming into Norfolk. As you say, weather, winds..crew capabilities, vessel, tend to dictate schedule.