I tow smaller (24 ft and 5500 lbs) than the OP, but I can say from my drive this week that the F-150 can be a good tow vehicle when set up right. Mine is the 2016 XLT 3.5 EB 4x4 with tow package (not max tow as far as I know - the dealer was changing ownership when I bought it and the new staff had far more expertise with Chevy than Ford).
I towed about 1300 miles over 5 days in stormy winds through Nebraska to central Iowa and back home to Colorado. While there were some interesting moments that took a bit of getting used to (semis passing on the 4-lanes), after a couple of days I was taking it one handed about half the time and having no issues.
You have about 6 more feet of TT for the wind to push on, so that gives you a bit of a disadvantage over me, but with the proper setup and a good WDH I don't see why it can't be done. The hills should be no problem at all.
As others have mentioned, payload will be your enemy. Tongue weight plus cargo adds up fast. I only use a little over 1/3 of my 1777 lb cargo capacity with tongue weight, so I have never really worried about that.