We just took our class C down from CT, great time!
Our timing, route and stop schedule is a bit different since we swing out into PA and drop into 95 just north of Richmond (84 to 81 to 17 to 95). We usually get a overnight campsites along the way, but we did successfully try our first "boondocking" overnight at a casino last weekend! I found it on the All Stays Camp & RV app. We thought about pushing through, but decided to just bed down for the night and campgrounds were all pretty much closed for the season in the area of Harrisburg and Scranton. So I'm no help with major experience boondocking, but we've stayed at the Americamp north of Richmond and found it to be easy on and off and easy to get a pull-through after dark.
Premium loop suggestions, we've stayed in 400 and 500 and we liked them both. Are you taking bikes? That's a sweet way to get around the Fort. We have never felt the need for a golf cart, but love having bikes along.
We also don't dinghy tow. By the time we are close to FL we've determined what we've forgotten and hit up a
Walmart or KMart along the way (there's a KMart in Kingsland GA that we like to hit for some reason) so we haven't had the need to dash out for something. I'm guesisng your C is relatively new to you, but the planning ahead is just something you'll get used to. You'll realize that there is very little that you don't have along or can't live without. Plus the Trading Post has a lot if you heed something like milk or eggs or anything. Of course you could always call a cab or rent a car, but you won't need to.
Happy planning!