Things have certainly changed along the Florida Pan handle as far as Marinas and fuel since 2004. If Smittypaddler had given me a phone call or E mail, I would have put him up at my dock, and even right after Ivan gotten him gas somewhere. In the Pensacola area we host many "loopers" on a regular basis--but the C Dories are one of the few boats which have shoal enough draft to get across a sand bar to our dock.
Please any looper, give me a call or E mail, we are in the phone book on La Pas street. We have transportation and know the area--will even round up some other C 'Dory owners as an excuse for a party!
Current status of the Marinas in Florida, is that some have gone the way of condos, but that is what is happening in Florida all over. There are still many places to anchor, and no reason to go to a marina, except for fuel and water. Even on holiday weekends, there are out of the way isolated places. Some marinas are pretty pricey, and there are C Dory members or other boaters along the way with docks who will help you out!
As for the Lower Mississippi. Talk about areas where you cannot get fuel. You have to jerry jug at Vicksburg--and there is basically nothing until you get to New Orleans (as it is reconstructed). I personally would want a good range--probably more than most 22 's carry, or spend a lot of time drifting/slow speed to get the range. Also there are stretches where there are no really good places to tie up for the night. I agree that there are some good day trips, if you launch and run up and down the river, but would discourage the average 22 owner from doing the entire lower river below the Arkansaw. I hope that the Tom Cat 255 will have enough fuel (we cannot jerry jug because of health issues) to do this run, but it can be tricky. I have done part of the lower Mississippi in diesel boats with longer range.
The Great loop (or Circle) is typically from Florida--in its full extent around Key West, or Hawk Channel, up the ICW, to the Hudson River, Erie Canal, to the St. Lawrance, Great Lakes to Lake Michigan, Down the Illinois. with a short stretch on the Mississippi, Ohio, Cumberland, to the Tennessee, then down the Tom Bigbee waterway to Mobile, and along the Gulf Coast ICW to Carabelle, the Big Bend, or cross the Gulf (can be some open water), to the ICW down to Ft. Meyers, and Okechobee Waterway, or down to via Marco Island Key West. There are a number of books on the loop. "Honey Lets get a boat". The Great Circle Cruise (Remmy) and Skipper Bob publications are some of the better books to start with.
So, Cosmic C, when will we expect you in Pensacola? You timing is about right--and don't let people scare you off because of hurricane season. There are always places to go which will give good refuge, if necessary. We were right on the track of Ivan--135 mph documented wind gust only 5 miles from our house at a military facility, and had no damage to our boats in the bayou where we live.