Steve you do NOT want it in the locked up position to haul. That tips it too far forward to chain down easily. With it in the down position the header skid plates will lay down flat on the trailer and is easy to chain down. The other way it is tipped forward and if you chain the frame like you think, the header will bounce the entire trip.
I would take the nut off the tongue bolt before he gets there and then lower the haybine to the ground. With it that way turn the bolt in frame to make sure it is not stuck. Then just put the nut back on with it lightly tight.
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