Seems no one else is going to answer this, so I will take a crack at it. I do not have a TT and therefore no WD hitch, but my next door neighbor does.
His immediate comment is that if you are having to lift any more than what the tongue jack will do, then your hitch is not properly adjusted in the first place. I have watched him hitch up and once the TT is on the ball, he lifts up just enough to allow him to hook up the bars, and that is not more than maybe 5-6".
Also a comment for clarification, a jack stand is just that, it is a stand to hold up something that has been lifted or jacked up. It will not lift anything by itself but they do have jack stands that can provide support to varying heights but sometimes you may have to place them on a block so that they can be run up high enough.
I admit I may be off base, and if I am, perhaps you could provide a more detailed description of the issue (with pics?) that might help clarify it for myself and others.
2013 Infinity 3640RL with Trailair pin box
2008 F-250 King Ranch Power Stroke diesel with B&W Companion Slider hitch