Let me qualify my statements first...
I've been a commercial truck driver for 15yrs (1.5million miles without an accident)

operating everything from a pickup hauling GN horse trailers and RV's, to semi flatbeds, lowboys, and refers.
Currently, I pull doubles (refers) in IN, OH, MI, IL, KY nightly and manage daily routing for the 40 drivers working for a mid-sized wholesale food distribution company.
In addition, my wife manages the service department of a large RV dealer here in Elkhart, IN.
My RV consists of a '07 F350 dually and a '03 39ft Alfa Toyhouse (I'll get a pic up soon)
Your reference to "triple-towing" is misleading, triples are a tow vehicle plus
3 trailers.
Triples are only allowed on limited roads (mostly the I-80 turnpike through IN and OH) and do require special (annual) permits and of course, a doubles/triples endorsement.
Pulling semi doubles only requires the driver have a doubles/triples endorsement on their license (no special permit/fees necessary) in any state that allows doubles. However, they are limited to designated truck routes (usually interstate/state hwys only) and reasonable access too them (secondary roads less than 10mi from major route) and each trailer is limited to 28.5' in length (Rocky Mountain and Turnpike doubles are exceptions), overall length is
COMPLETELY IGNORED 99.99999% of the time for doubles,
it is only enforced on trailers over 48'. There is NO overall length limit for single trailers under 48' (the tow vehicle can be any length as long as the trailer is less than 48') which is why you see tractors with apartment sized sleepers driving around, they can only (legally) pull a
<48' trailer.
Pulling a boat behind a 5r is common throughout the midwest, I have pulled double GN horse trailers (with a dolly) into FL, but I was operating commercially.
From my observation, non-commercial doubles are legal virtually everywhere (although I'd stick to the truck routes) I've not heard of anyone being forced to separate a 5r from a boat or small utility trailer or getting a citation (unless they were grossly overweight)
The previous poster's pictures of his rig are a good example of what I see almost daily throughout the midwest.
Special attention should be paid to the GCWR (Gross Combined Weight Rating) of the tow vehicle when pulling doubles, exceeding that limit could lead to liability issues in the case of an accident (or draw unwanted attention from Johnny-Law)
BTW, I'm not a big fan of swivel wheeled add-ons; they promote trailer overloading. Most RV trailers are barely adequate to handle their own weight plus personal items, water, propane, batteries and the frames on most RV trailers (toyhaulers the obvious exception) aren't designed to carry a load behind the axles, or capable of dealing with the torque applied from turning with an extension dragging a (unreliable) swivel wheel (by unreliable, I mean they don't always behave or rotate the way they are designed)
As long as you're pulling a GN or 5r, a second trailer (with brakes) would be a safer option IMO.
BTW, double bumper hitched trailers are not legal anywhere (before one of you beer drink'n rednecks get any ideas

)