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1. One air conditioner will work fine in Fort Myers in the winter. In the summer it would be iffy.
2. If you are staying in a place with hookups you won't need a generator.
3. Any 3/4 ton diesel will pull the 29 just fine. See my signature. I am prejudiced, but go 4 wheel drive. Some of the frame and driveline components are a bit heavier and you may not need it much but when you need it you will really need it. I use it in very heavy rain just for insurance. Just for reference, the 2955 RL is 32' long. When I am hooked and loaded for travel my combined weight is 18,600#
That trailer has approximately 4' more useful space than a 32' motorhome and it is significantly less prone to wind gusts and sway. There is a learning curve to hauling it but the curve is short. Take it to a large empty lot and practice.
Enjoy
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