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Jacking the trailer via the chassis did relieve the pressure on the bolts/bearings and allowed me to get grease in. Since the chassis is 24in from the ground I had to build a "jack tower" from 4X4 blocks. With an 8T bottle jack there was just enough lift to get the wheels almost off the ground which was enough to permit the grease to flow. I suspect that once the bearings wear a bit it will allow the grease to flow in more easily.
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