Okay so there is probably more to this story than I originally layed out for everyone...
The trailer used to have 14" wheels and much smaller tires (think standard trailer tires). So in the old picture the ball and hitch did provide a level hookup and tow which was desirable. If the ball would have been flipped the trailer would not have been level and the rear end of the trailer would have ridden closer to the ground due to the trailer tilt - which would have made the rollers just as difficult to clear.
Since the first picture in the woods was taken though, the trailer was upgraded to run 265/75/16 tires as pictured... After making this change to the trailer, the coupler height need to change as well.
So from all this...my desire to to do a hitch flip solves two issues:
1) Raises coupler height to match the new tires on trailer for a more level tow.
2) Improve ground clearance by changing the low point on the hitch.
Thanks for all the feedback guys.
A different stinger alone though would not improve ground clearance as the lowest point on the hitch would remain the same (more likely to dig or get hung up).
And an aftermarket hitch, while it would raise the low point on the hitch about 3", would only add 3" of coupler height.
Hitch flip adds 6" of coupler height and 3" ground clearance.
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