A 5'er will be less cost than a truck conversion, even including buying a used HDT to pull it; assuming approx equal used comparison. Most 5'er toy haulers are not set up for a car, they don't have the load capacity or garage length. Good for couple motorcycles or a UTV or golf cart and some misc supplies. Even the big 3 axle are not intended for full car. They don't have the load and they don't have the ramp capacity.
HDT has sufficient load to haul a car and the tongue weight on the truck. That pic you showed is likely just because of length, not hitch load. Look over on rv.net and they have a HDT section that has people with better experience with the HDT pulling a large 5'er. A simple solution for the car is just have your wife drive it following behind. Then you can use a shorter single axle HDT truck.
No clue on what IL rules are. Knowing how IL seems to be on most other stuff, I am sure it will be bureaucratic process at it's finest.
Any conversion you build yourself for a car length garage will most likely need a frame extension to get the wheelbase required, unless you find a long one by luck. I doubt you could build one for less than you could buy used, even not factoring in your labor as any cost.
Overall, you are talking a huge cost increase either way you go vs your current class C. I think you will have significant sticker shock, but understand that a bigger living quarters would be nice for the family and your ability for full timing.
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