We have made the trip to and fro several times in a larger, deeper draft boat, anchoring in a wide variety of locations and mooring (Vero) all along the way. Yes, it would be good to know what your experience level is. Another very good on line resource, that I personally prefer to Active Captain, is
Cruiser's Net.
It is little better vetted than AC. and for me easier to use. A copy of the Waterway Guide Southern and AICW editions is also excellent for planning purposes and a little easier to navigate than the on line stuff.
Have you practiced picking up a mooring single handed? It can be darned tricky if the wind and current are working against you. Anchoring is generally easier but again requires practice for any particular boat. Although you don't plan on it, also practice docking and undocking the boat both with and without on-shore help, floating docks especially but fixed too if you have the time; the best fuel stops along the way are fixed/bulkheads by the way, or you may have to make an emergency landing after hours... things happen!
Also what is your plan for when nature calls? For meals and beverages the 390 (we chartered one a few times) is a nice set up since it is all right at the helm, but advise having the day's plan for eats and drinks organized before departure.
Agree also that dawn-to-dusk is inadvisable, both from a stress standpoint especially if you come upon a destination at dusk where you can't find room or get a good set. Now you are hunting around in the dark. Give yourself plenty of time to find a good spot and relax. It will only add a day or two to that relatively short trip. It is a fun a pretty trip, so why not enjoy it a little. Ditto on a tow company membership for absolutely sure. Even if you don't need them, they are very helpful providing local knowledge.
Why don't you put together a draft itinerary and let some of us vets advise from there?
Then, make sure you file a detailed float plan with someone reliable and check in with them regularly during the day. Cell phone service is generally very good along that stretch though it can get a little sketchy in spots.
Have you considered including a weekend so helpers can come join for a day? It is not a very long drive; one can deliver a crew mate and then shuttle the car to the next pick up point. Regardless, this can be a very very fun adventure with proper planning.