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Hi Charlie, Suggests something amiss with the bead area of the rim. Just a guess but seems running down the road aggravates the issue then parking it leaves the bead displaced allowing air to leak out. If I were you I would have that tire removed an very closely inspect the bead seat for scratch or something that is partially across that area...refilling the air may push the tire out against the rim allowing it to maintain pressure...moving the trailer must push the bead to a compromised location and very slowly you loose pressure but only on parking...total speculation here but maybe someone else has better theory.
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