Now that we know what we're up against, it's time to make it happen... Step one, remove the offending headache rack:

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With a clean slate, I took several factors into account such as the lid of the toolbox (which only opens to about 45* by design), the swing path of the deck latch, the theoretical location of the tie-down straps as they run from the tongue anchor point up to the tire strap, and the desired minimum centerline location of the front JLU-R XR tire to get the tongue weight we need:

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After a couple of iterations and perhaps and adult beverage or two, I settled on the best location I could pharmer up for the new headache rack cross beam. The factory headache rack was built using 1/8" box tube components, and didn't weigh much in the grand scheme of things. In my quest for as much tongue weight as I could muster, I searched for the heaviest material I could find, and that came in the form of some
heavy wall tube:

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I then carved out some simple offset stanchions that provided as much weld area as possible to the trailer frame:

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Then I put some heavy tacks on everything:

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And gave it a test load to see where things landed:

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Yahtzee!!! We are roughly 1/2" further forward than necessary, and given the redesign of the headache rack itself using beefier materials we've added at least 50lbs of additional static tongue weight
It looks perfect on the trailer now, and I also verified the strap configuration doesn't interfere with the new headache rack:

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I pulled the trailer back in the shop, threw booger welds everywhere, and lathered on some fresh enamel paint:

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