The purpose of a WD hitch is to transfer some towed weight (from the tongue of the trailer) from the rear of the towed vehicle to the front of the towed vehicle. (TV) This is to even out the tongue weight of the trailer on the TV. So the TV's rear end does not drag. YOu do not have this typical issue towing, as you are not towing any where near the limit.
Your TV was designed to take a ton of weight on the rear. Literally!
If you want to use the set up to reduce sway, that is another matter. However the WD part of your hitch set up is not necessary. In fact by transferring more weight to the forward portion of the TV you may create a problem.
Based on your pics and description, you do want to level the trailer. Or bring the front of the trailer up in the hitched up postion.
1966 Mercury Park Lane 4 DR Breezeway 410 4V, C-6, 2.80 - Streamless.
1966 Lincoln 4 door Convertible 462 4V 1971 Ford LTD Convertible 429 4V Phoenix ~ Yeah it's hot however it's a dry heat!