Originally Posted by SeaDog
Welcome to the forum its a great place to get your questions answered. You didn't say what your tow vehicles is that can have a real bearing on WDH or no WDH. It may be that with a trailer that has a gross weight of around 3800 lbs and a tongue weight of about 300 a WDH is really not needed.
X2. Does the HW276 use a 2" ball? If so, I wouldn't think a WDH is necessary. We pull a 7,000 lb cargo trailer without a WDH because it is not required. That's about twice the weight of your new popup.
What I would suggest is adding load leveler type air bags to the rear of the Rubicon. They will do nothing to increase weight capacity, but they do wonders leveling a load, road stability, and much more comfortable ride. They are cheap and easy to install. Check "Air Lift 60817" fits rear of Jeep Wrangler.
2007-2017 Jeep Wrangler 2WD & 4WD - Air Lift 1000 Air Helper Springs [REAR]  | $81.63 | SD Truck Springs | Leaf Springs, Helper Springs and Suspension Parts
Your TT dealer should be able to give you a ball height for the trailer. If you have a ball on your Rubicon, measure that height and determine the drop. You should be able to determine the necessary hitch drop doing simple math. My guess is that it would be a 4 to 5 inch drop. On our son's Liberty, we use a 5" drop to clear the bottom of the spare tire.