Does your work have any other trucks that might be used to relocate the trailer? Many times you can ask the supervisor and borrow a 3500 or even a F-650 to move a trailer, then bring it back the next day, and get back into your normal work truck. Or you could consider renting a F-650 from U-Haul to move the trailer, then bring the u-haul back and get your truck and go to the trailer next location.
You would be really limited by the F-150 as a primary mover, especially in the middle of a snow storm. I would not want to move it on a day with ice on the roads, no matter what tow vehicle.
I lived by myself in a 30' Bounder Motorhome. It had 'enough' room. My buddy had a 31' Terry Travel trailer (not suitable for 0F weather camping) and it had a front queen bed, and convertible couch, and dinette table that made into a bed as well. I guess that one will get the bedroom, and the other is stuck on the couch, so making breakfast might wake them up, unless you both have the similar work schedule?
Personally I would not try a roommate in less than a 30' travel trailer. It will get awfully crowded on a long winter night in such a small space, and you are not able to get out and take a walk to get some 'space'.
You will need a few propane tanks. Skirting will help, but it sounds like you will be moving the RV a lot?
Artic Fox sounds like a good brand, suitable for your needs, and not freezing at night. You might also consider a Olympic Catalytic heater. It provides a constant 6,000 Btu's of heat, so you do not need to listen to the furnace as much. It also does not have a fan, so it is silent, and can run if you lose power.
Good luck!
Fred.