Honest Rob, the reason why Cruise American rents campers without jacks is because taking them on and off a pickup is sometimes not easy. Accidents do happen.
In your case, you have a lightweight truck, shortbox, crew cab and a torklift extension and heavy engine. Your carrying capacity is fairly limited, there are few campers that would allow you to do what you want while you tow your boat. (What's the tongue weight on that?)
But best of luck. I would think if you want to test camper living, rent the Cruise America unit and try it out.
Study your weight capacity, your tires and wheels, weigh your unit with your extension and boat connected, loaded with everything, and truly see if you have much capacity left on your rear axle. Remember, it's fairly easy to stuff 1000 pounds of your own gear into a camper, so that F250 gets overloaded fast.
Mike
2012 Winnebago Impulse Silver 26QP
2005 16.6 Double Eagle
2018 Jeep Wrangler JK
previously Snowbird Campers,
Triple E Motorhome and Fifth Wheel