I have had a 5th Airborne air ride pin box for 10+ years. I air it up to the line after I first hookup in the spring and never let air out. I may have to add a little a time or two during the travel season to get back to the line.
I have a Reese Elite hitch with the wrap around jaw and there is never a problem hitching or unhitching with the pin box aired up. Had a Pullrite Super 5th hitch on my previous truck, also with wrap around jaw, and never a problem with that one either. The pin box plate rocks forward and aft and self aligns with the pin box plate as I back into it, or when I pull out to unhitch. The pin box plate should be an inch or so below the level of the hitch plate so that the pin box rides up on the hitch plate to ensure that self alignment and easy hitching. Or down off of when unhitching.