CC; not doing this any more but when we were, it was with an IH 4400 530E full air, ten spd, a Gearmaster, 3:08 rearset with a GeneMcCall AirGlyder hitch with a Trailaire Pin box and if memory serves about 3400 lbs pin weight from a 38' Mobile Suites.
Running both the Trailaire and the Airglyder never once caused me any cyclical bouncing or dampening conflict. I had a Voyager two camera system with one camera mounted on a tall light tiara built behind the Harley barn on our truck looking down at the hitch area and it was a marvel to watch the trailer floating along sedately while the truck was giving our kidneys a beating,
You have a triple axle set up which should help mitigate "chucking" but that new design air pin-box looks like the arc of travel of that floating underplate would be about 6" from the pin to the center of the cross pivot bolt. I'm thinking that braking events would cause the trailer to forge ahead with that plate pivoting rearward along with your pivoting head of your truck hitch tilting forward making for some extra fore and aft movement until trailer brakes take charge. Not desirable with front cap so close to Jeep.
My other concern would be to keep a very jaundiced eye on your goose neck framework. Long-snout pin-boxes put enormous leverage on framing of heavier pin weight frames.
A Go-Pro Camera is going to give you very useful info indeed for future decisions. Mounting a flexible fiberglass stanchion screwed to a good plate magnet at the point duplicating your jeeps furthest rear point and mounting your Go-Pro to the side so it can see the interplay between the trailer and that stanchion while you put your rig through it's paces with curb, parking lot, driveway, transtions etc., might avert a later disaster.
PS. mounting the Go-Pro so it can view the gap between the top of your pin-box to underside of trailer cap might just cause you to assess the amount of frame flex going on under there as well. Just to be careful and pre-emptive.
Nice build-up and very enjoyable to read about. Good luck.