Hey Advocate,
I did this trip a little over a year ago from Hampton, VA to FL, and all I can say is don't worry too much about it. Spend time planning, but really it's very do-able. I spent the night before the trip in Norfolk and headed out early the next morning (around 4 am). I made it to Beufort, NC 4 days later. It was a great 4 days, I did that part solo.
A friend met me in Beufort (pretty cool little town by the way) and we went offshore. I was sailing down because I was moving to Florida so I was unable to pick my timing like you are. I ended up going in July and passed everyone as they were heading back up north. In any case we spent about 80% of our time under power or just ghosting along with a 5 knot breeze. There was one night where it kicked up to about 35 knots, but even that was managable.
I didn't see too many places to pull in for the night once south of Beufort. I'm in my office right now, so I can't really pull up any charts right now, but I'm sure there will be someone along shortly to correct me if there are inlets south of Beufort. I ended up pulling in to Charleston after 3 or 4 days.
It was pretty light offshore work, and it was a great trip. You didn't mention what boat you are going in, but I would think a reasonably well maintained, moderately sized coastal cruiser would have no problem with this trip.
Feel free to PM me if you need any more information.
Good luck, and most of all, have fun with it.
oh yeah, and as mentioned above:
www.activecaptain.com is a GREAT resource