Bones, that is quite the plan. Good luck! Make sure that you get your permits for Everglades National Park at either Flamingo or Everglades City (Choko)
You may want to consider Marco Island to Choko, but stop to scout Panther Key and other Islands just outside of the Park boundaries just so you can get a feel for the low and high tide appearance of these areas before you encounter them in the EC. Maybe leave Choko and head out and in various Passes to learn your options.
Try running against the tide in these Passes so you will learn what to expect, and how to make progress in the event you must move against the tides here.
I have Florida Bay photos online from an out and back out of Flamingo to Key Largo. Click here to go to Florida Bay Loop at photobucket.com/scareman. I went the Southern route out, and back along the Northern route. I left Flamingo at a low tide to see what it looked like and also feel the effects of the ebbing tide leaving Florida Bay as I left. Flamingo. After a good day's paddle-sail, I landed at the Finish after sunset, I ordered spaghetti at Mrs. Macs, went across to CVS to freshen-up, then back Mrs. Macs to get my dinner, then ate dinner at the Finish at the picnic table, then off to North Nest Key for camping. The next Day I returned to Flamingo via the Norther route over Crocodile Dragover.
If you plan to rest at a Chickee, then you should make sure you can land with your vessel and get what you need while leaning over a platform or hanging onto the ladder. Many ECers lift their kayaks onto the chickees while they wait, but I leave my tandem tied-off in the water while visiting a chickee.
Get out there at night, against the tides, check out landings at both high and low tides because you will be amazed what is uncovered. This knowledge will help you decide when and where to land in your journeys.Tou may be amazed at the flats that leave you hundreds of yards high and dry after you wake up to a low tide. Maybe you will discover submerged trees at beaches during low tide.
Keep us posted!