I have flown and tent-camped before at Ft. Wilderness and it is most definitely possible.
Most airlines allow 2 50lb checked bags (check your airline website for maximum height/width/depth), then 1 carry-on bag (such as a rollerbag), and one personal item (such as a bookbag/computer bag).
Southwest allows 3 50lb checked bags.
As a solo person I bring the following:
10x10 tent
10x13 shelter
folding arm chair
air mattress
sheets/blanket/pillow (Electric Blanket in the winter)
Small Fan
Battery operated hanging lantern
Electric air mattress pump
ground cloth
disposable painters plastic to put under ground cloth (throw away at end of trip)
Laptop
Digital Camera/Docking Station
Alarm Clock
Cell Phone/Charger
Power Strip
40 ft Outdoor extension cord
3 days of clothing
Laundry Detergent
Dryer Sheets
Toiletries
Towel
Washcloth
RainGear
Shower Shoes
I pack it in a plastic locking footlocker and an extra large duffle bag (need the length for the chair) The lock is to lockup the laptop at the campsite, don't lock it for the flight. I also have the roller bag as a carryon and a bookbag to carry toiletries to the comfort station.
If I'm flying Southwest, instead of an air mattress, I can bring a collapsing air cot. (However flying and camping on Southwest was more trouble than the extra 50 lbs allowance). They had a "really" great airfare, so I had to try though.
I don't cook at Ft. Wilderness, there are too many good restaurants at WDW.
If you use Magical Express, try to fly with a "participating airline" and fly at a time when you can use "Resort Airline Checkin".
Also try to have someone drop you off/pick you up from your home airport.
The reason SW was not worth it for me was as follows:
Southwest is not in my home city, Southwest does not participate in "resort airline checkin"
So, I drove to the city where Southwest was, parked in remote parking.
Tipped the shuttle guy for helping me load 3 50lb bags in his shuttle
Tipped the skycap for helping me check 3 50lb bags at curbside
The bags were then delivered to my site by Magical Express, no problem there.
For the return:
Tipped the Ft. Wilderness guy for getting 3 50 lb bags back to Reception Outpost for storage.
Tipped the Magical Express driver for 3 50lb bags back to the airport
Tipped the skycap at MCO for helping me check 3 50lb bags at curbside
Tipped the skycap at Nashville for helping me move 3 50lb bags from baggage claim to the remote parking shuttle
Tipped the shuttle driver for helping me move 3 50lb bags from the shuttle to my car
If you fly a participating airline from an airport where someone can drop you off and also use resort airline checkin, you can avoid many of those tips to have folks help you lug your stuff.
If this sounds all too complicated, PM me, and I'll try to explain.
I hope I've been helpful.
