No offense, but:
You lost me when you described hauling your truck 4 FEET in the air, by the hitch, last time. And please tell me you
have a Class IV hitch? (If you did already, sorry, I missed it). You're not using a bumper-mounted ball, right?
I'm sorry, but this can't end well, IMHO. Have you considered how a rollback is going to deal with loading up, on the side of the road, if there's a shoulder, and he's not level? When the low side tires of your trailer are the ones that blew, making the pitch even worse? He may not likey.... Traffic whizzing by, etc....?
I have Sirius XM, so I think I can get local news, anywhere. What is your zip code?
And I think $1,500. is an optimistic figure, to R&R an auto trans, and repair/rebuild it. Where I live, you can add another $1,000. to that figure, easy. Did I mention I try to drive sticks as much as possible?
It's rollback time, IMO, my friend. You can ride along--it's air conditioned.
Enjoy the ride--it cost LESS THAN ONE TIRE. And if you overstress these trailer tires now, what if they don't blow until NEXT time, on some long trip/vacation, etc.... Potential delayed saturation bummer....
Good luck.