You asked about flat towing prior to mentioning towing it behind your 5th... I never really was 100% comfortable flat towing it but I was resisting buying a trailer. After I smoked the t-case I didn't have a choice.
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I pulled doubles & triples when I was a OTR driver so I honestly have no desire to with my RV. But for a lighter load like a SXS or ATV or golf cart type load I can see the logic. But for a heavier vehicle like your LJ or a TJ I'd have to pass on the idea.
Sorry for the confusion. I have a flatbed trailer to load the LJ on if I want to pull behind my truck. Flat towing behind the 5th wheel is what I'm considering. Doing some research on the hitch setup for the 5'er... there's a lot of folks on a "Double Tow" group who've beefed up hitches and put lots of miles on them that way (both flat and trailered). Not arguing the point, we all have our comfort zone, and I understand "just because you can, doesn't mean you should".
Unless I can train my wife to be comfortable towing the LJ while I tow the 5'er. She'd be fine, has towed ATVs and stuff but still might be nervous.
Thanks for putting up with my ponderings.