I'm not sure about summit racing's cheap black 16.5" rims as most of them are only rated around 2,000 lb each.
Basically soon as the truck get hooked to a trailer with the jeep, the wheels' "overloaded".
In the pic, do they rub? Look like no lift. What wheels are those in the pic?
I did some searching on those military 37's and I found that some said they mostly measured out to be 35"-36" tall. So if that's the case, that'll help with the fitment and towing power over true 37" tall tires.
I might gonna try the stock double beadlocks H1 rims with spacers if I still can't find rims I want with good load rating and proper backspacking.