Not only is it legal in WI, but as of 2012-ish I don't even need a permit. But there are rules, don't get me wrong. Overall length, within combined gross weight, the second trailer must be a recreational trailer (boat, ATV, motorcycle...etc...empty or loaded) for example. There are a few more.
It is legal in many other States as well. But for other States I haven't come across one that separates 5th wheels from TT's, not to say one doesn't exist.
The only separation I have come across is allowing people in the trailer. Some states allow people to travel within 5th wheel TT's! CRAZY!!!
Unloaded, the TW is about 400lbs, and it drops the rear enough, but not major. Driving without the WDH is horrible compared to with it applied. HUGE difference.
I have towed double single axles around town but not on a long trip.
Mexicans tow doubles all the time around these parts. Usually two flat towed broken down vehicles behind a slightly less broken down vehicle.... Your set up is miles better.
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