In my experience, the average Section 8 resident behaves differently than the average market rate resident, and the government-backed rent is not worth the added hassle.  

I've owned student housing as far as 4.1 miles from the University of South Carolina campus.In my experience, the only reason kids would live that far away is cheap rent.

But I find from personal experience and from my buyers' Airbnb experience that it's a bit of a hassle trying to get guests to rebook at the new listing.I don't know how strict Joshue Tree is at enforcement, but in Denver and Colorado Springs here, you could probably get away with an STR listing for three months without the license.

I'm wondering if that might be less of an issue for something more rustic and temporarily occupied like camping/RV.Any one have any thoughts, parallel experiences, or other basis for insight? 

Jorge Newberry is the principal and a very good guy from my experience.

It seems like you are either taking bad experiences that you have had, or things you have heard, and you are blanketly applying it to entire strategies that have worked and been helpful to tons of people. 

If so, any one have experience doing so in a way that does not accumulate a lot of transfer fees?

There may be other issues at play here that have little to do with a lack of experience at real estate tech platforms. 

Secondly, you'll definitely want to confirm with a tax strategist with experience in the STR space to confirm if the setup you describe will pass as an STR with the IRS. 

Start local and small, then grow from there with experience.