Robert,
I can comment on Cape May south and leave the northern leg of your proposed trip to others. I try not to go north of Cape May after October 1.
Books, etc.
You already have two of the more popular books for ICW transit, The Moeller's
ICW: Norfolk to Miami, and Skipper Bob's
Guide to ICW Anchorages.
The Maptech Chartbooks are best for use on a small boat and probably the most economical. You'll need:
Region 4,
Chesapeake and Delaware Bays,
Region 6,
Norfolk to Georgia,
and Region 7,
Eastern Florida.
A useful addition to these is one of the many so-called "Cruising Guides" that give the telephone numbers of the many marinas and other facilities along the ICW. The phone numbers are mostly to call ahead for slip reservations instead of using the VHF for this.
One of the more useful ICW real-time information sites is Claiborne Young's Cruiser's Net. Check it out at:
http://www.cruisersnet.net.index.php
You can also log into the relevant USCG District sites and get current Notices to Mariners. Most marinas & other businesses have hot-spots so you can use the 'Net while enroute so doing this is pretty easy.
Best time of Year:
Fall, without a doubt. Get south of Cape May before Oct. 1 and into Florida before December.
Time Frame:
The one thing that ruins the pleasure in a trip like this is a rigid schedule.
Get-there-itis also causes a great many misadventures -- people going on when they should hole up. From Norfolk southward it's relatively easy to plan travel days with the Moeller book. North of Norfolk your day planning is primarily weather dependent. Normally I'll do the entire Chesapeake non-stop and treat it almost like an offshore passage. Also, it is nice to do a few point-to-point offshore legs when the weather permits, especially around places that are a PITA (like Florida south of Lake Worth). I suggest you sit down with charts, Moeller, STD info according to your preferences and rough out the entire trip. You will never acheive this, however, unless your crystal ball is 100% accurate, but it gives you something to plan against. Count on spending some days at anchorages/marinas due to inclement weather.
Safe To Single Hand?
That depends entirely on your confidence level. You may want to contact Bill Watson aboard
Kittiwake (CD-28) who has been doing this trip (at least from Annapolis area) for the last three years. He is a wealth of information on all of this.
Budget:
The previous poster covered this well. If you can stay on anchor as opposed to a marina then the cost is mininmal. I generally hit a marina every 3 or 4 days to wash clothes, resupply, eat someone else's cooking, fuel up, etc. This is another of those "point-of-pain" things with many people. I've done deliveries with people who had to be in a marina every night and other deliveries where we never stayed a single night in a marina.
So, there you have it, at least for the questions you asked. Plan it out and go. It is easier than you think especially with your usual attention to detail.
________
Rolling A Joint