Thank you for all the responses and advice. You guys gave us so much more information that we never thought to ask about. We will definitely get the trailer brake control added by the dealer or get an aftermarket one.
I have looked up the answers to your concerns and advice:
Per the RAM website, the truck will haul 11,400 lbs, has a 1,500 lb payload and it's a 4WD. It has a Class IV receiver-hitch, 7-pin wiring harness, and 3.92 rear axle ratio.
The trailer has 2 sets of wheels on each side (dual axle) and weighs ~2,000 lbs and will tow 10,000 lbs (per the dealer). It does have trailer brakes.
The MX5800 has loaded tires, FEL and will either have an 1,100 lb brush hog or a 900 lb
chipper (hopefully an EA grapple in the future), so I think I'm close with the 9,000 lb tractor/trailer weight estimate.
The drive to the property is primarily flat with only a few curves on the back roads.
We will definitely be doing an unloaded dry run with the trailer and be sure to level out the load. Do you have any recommendation on trailer hitches besides getting a Class IV and 10,000 towing weight?