Very good advice so far.
My truck is almost like yours. Its a '96 F250 7.5L, C6 trans, tow package.
I pull an 18' bumper hitch flatbed thats normally between 4000lb and 7000lb. It took a couple of adjustments to get the hitch height where the trailer was close to level with my different weight loads. Also if I get caught in the rain, starting out on a slight upgrade can be a challenge since I currently have open diffs in my truck. Truetrac going in by the end of the month.
My trailer doesnt catch the wind like yours will. I used to have a 24' enclosed and the wind will push you around.
Like others have said start out slow & easy and get the feel of it