I think you'll be dead in a ditch surround by flaming car and trailer the first time you have a panic stop
Just going downhill will likely make a neat pyramid shape in the middle of your drivers seat.
Tongue weight is IMPORTANT. I used to tow my samurai to and from trails, both trailered and flat. Even though the trailer weighed a ton (figurative) it was easier and more controllable than flat towing the light vehicle. As you stop the tongue weight helps among other things, keeping pressure on your rear tires. Flat tow, no tongue weight you just have an extra several thousand pounds trying to push through your vehicle. If your tow rig is heavy enough, it might not matter that much. An f150 isn't heavy enough to not matter.
The way most tow bars are set up on a hard stop you may actually have the flat tow putting upwards pressure actually reducing weight and on the tow vehicle. Plus it will be fishtailing like crazy.
So then strap a cargo trailer behind the vehicle that has too short a wheelbase to actually tow with and is overloaded by the weight of the trailer and what you basically have is an extra 8k+ pounds of weight being flat towed with an extra hinge in the middle, being pulled by a vehicle that is at/near/over tow capacity to start with. Besides being likely several kinds of illegal it would likely only go ok by pure luck.
I've towed a boat with on my of YJ's even though it was under weight, and tongue weight was 'proper' it was a total nightmare going downhill. It was scary if you were on flatground and had to stop quickly. It was several magnitude of sucking.
What I'm aiming at here: Doing the truck/jeep/trailer thing is a bad idea.