I can tell you after completing the first phase of a private RV park in SW KS - possibly the easiest place in the country to build - that you will find it very, very difficult to jump over the governmental, power company, water company, EPA, etc hurdles that are now in place. It is a daunting process, especially in any place that has zoning....where we built does not. And it still was not "easy". But it is possible.
Lots of good opinions here, and even some facts
On the "quality" issue, comparing a higher-end DP to an HDT/fiver, I'll express my opinion. Some would say facts. I'll leave that up to the reader.....
You can get into a NEW custom built HDT that will act as a motorhome for short trips, have every luxury, amenity and capability as a high end DP, and be about as comfortable (although not quite the ride, but close). When I say every capability I'm thinking of driving capability like lane keeping, automatic braking, cruise following, etc. Then pair that with a NEW custom built 5th wheel that will have every amenity, comfort and capability as a DP. Every single feature that a DP has the 5er will have that and perhaps more. It will also have more interior space, a higher ceiling, deeper slides, bigger windows. It will have equal or more exterior storage, although laid out differently. It will be custom painted and color matched to the truck. All this will cost you 1/3 LESS than a comparable DP of the same quality. It may actually be less than half, depending on who you compare with. It will not be cheap, however.....it will be in the 500,000 range. And easily comparable to a King Air or that ilk at 900K. You will not find these at your local RV dealer. They will have to be custom ordered, and custom built. But at least you get everything to YOUR specifications.
All that is well and good, but it does not resolve the issue of a "runaround" car. A smart is the obvious target and works well for some. A Fiat 500 is a very good second choice but it makes the truck a little larger. There frankly is no good solution for a Rubicon 4-door. There are "possible" solutions, but IMO they are not "good" solutions. Thus, with that set of requirements a DP wins every time.
Our receiver is only a year old, a power issue took the old one out. I was even able to get a new 211K from a dealer in Texas. The only thing I've found with the Pathway X2 is the travel time from 110 to 129 is longer than the Tailgater.
I would dare state that any unit thrown together on today's assembly lines are troublesome. You might get a good one but that would likely be an exception. Hast makes waste. Proven fact. We we're so disappointed when we were shopping that we sought out older high end units.
A Jeep would be carried at an angle and truck stay tandem. This would have eliminated us having the storage we have now. Also we personally don't care for them. The Smartcar better choice for us. All these choices are different. No wrong way, just what you are content with.