I would say your total weight is going to be 9000 to 10000 lbs, that’s tractor and trailer. Properly loaded you are ok as long as you do not have much other stuff or people. You need a 10,000 lb trailer. Ford is very clear, any tongue weight over 500 lbs or trailer over 5,000 lbs needs a WDH. For a short trip is it mandatory? Your call.
If you have the backup assist you have the trailer package. It may or may not include a brake controller. Fords factory controller is great, you can add it very easily.
I have the same year truck, super cab, 3.55 gears, 5.0 engine, and what you will be towing if you get the bigger tractor would be the upper limit I’d say.