Turns out my regulator was just set way too high for the air shifter. Looked at the gauge and it was pegged past 200 psi. Dropped it down to 140ish and the leaking stopped.
Took it for a test ride and it worked perfectly, even from 1st to 2nd full throttle where the r1 never seemed to work right for that shift.
Got the Pit Bull Trailer restraint all mounted up on the trailer last night. It's pretty slick as it doesn't compress the suspension or anything and can take the mounting parts off so if you want to use the trailer for something else you don't have a big motorcycle stand in the way.
Might still mount a chock that would be easily removed after I take it for a test spin if the front tire bounces around
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