Yeah, the safety of flipping a drop is really what is in question... I know the towbar needs to be flat but is it safe to raise it that far off the truck to make it happen?
Am I going to be forced to mount them under the bumper for it to be safe?
Some "drop" hitches are not designed to flip over. Most adjustables are designed to be rise or drop.
I know @Wildman suggested going with a solid one piece that can be used in either configuration, and it would be the ideal way to go, but finding one that is the exact height (+/- 2") you need might prove to be harder to do than you'd think.
As for the reasons you don't want high angles on a tow bar.... With your setup, the front of the Jeep would lift and try to pole vault over the hitch and into the back of your truck. If your Jeep was lower than your hitch ball, then it would try to jack up the back of your tow vehicle.
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