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Okay, it sounds like you have your mind set to do it. I wish you the best of luck in your journey/adventure. If you need any help near Oklahoma City, let me know.
I still think you will be much better off to sell/trade the M925A2 for a M915A1 or even a commercial road tractor. If you plan to resell the trailer, do the same with a truck. Might even be easier to sell as a combo if you go with a civilian truck. Get one with a sleeper and you might just...
How tall is your trailer from the kingpin to the top? If it is a high-cube van, you might run into height issues with either type of 5th wheel on a M925A2 with 14R20 tires.
I would like the idea a lot better if you had a M931 or M932 tractor, instead of the cargo and dolly converter. Then again, I think a M915A1 is the only truck I would move a 53' full of stuff with for thousands of miles.
Are you planning to drive these or haul them? Either way, make sure you paperwork is in order. I have heard from a few friends that had run-ins with the popo in Kansas when bringing trucks back to OK. Good luck with your recovery and trucks!