I think the IN regulations are pretty much the same as the IL regulations. You could buy a used HDT for less than a good dually make the minimal conversions and then trade up when the time came.
I think the most difficult part of the conversion process is the potable water and holding tanks which you don't need with the toy hauler.
For my 2 cents worth, a generator, provsions for shore power, seperate heat and a refrigerator would be the simplest way to accomplish that.
Doing the O/O thing would be okay, and the way to do it is probably just hook up the toyhauler and head down the road knowing that you probably need to at least "pass through" the weigh stations because the tractor is a registered commercial vehicle. If you did that, the truck and associated expenses would be tax deductible so you would have a cheap tow vehicle from that aspect.
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