A couple quick pointers:
You do not want "even squat" when adjusting the WD hitch.
The ultimate goal for adjusting the WD hitch is to return the front wheel wells of your truck to the same height as they are when the truck is unhitched.
There are two ways to get more pressure on the WD hitch: 1. Add washers to tilt the head back. 2. Take up links in the chains.
Why would you do one over the other? On most WD hitches you want the bars parallel to the trailer tongue with good clearance so they can pass underneath in a turn. If the current chain length does that, you need to tilt the head back to put more pressure on the bars.
In your case you will probably need a cheater pipe to latch up the chains even with the trailer jacked up.