Got my replacement wheels in today and installed. It sure is nice to roll the trailer around again.
Doing some more thinking, I think I need to have the high point on the air shock on the trailer side and the low point on the hitch side. This should allow dampening almost immediately as the trailer pitches up/down. With the trailer side low and the hitch side high, the trailer would be able to oscillate a few degrees before the shock would be able to engage it's dampening. That sound about right?