Setting up an LLC for each property would make little sense because the cost per entity would be prohibitively expensive.

@Matt RedmondTo learn more about the prohibited transaction rules, see the following. https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-prohibited-transactionshttps://www.irs.gov/retirement-plans/retirement-plan-investments-faqs

Some states and counties actually prohibit discriminating based on source of income, like child support, alimony, veteran’s benefits, etc. 

What about your current vocation prohibits you from qualifying?

And there is a clause saying that anything not listed is automatically prohibited (a white list). 

Eric,you can't personally benefit from your IRA, that would be considered "Prohibited Transaction".

Wouldn't it be a prohibited transaction and/or an unqualified contribution to pay for it personally? 

Currently, short-term rentals are prohibited in the residential zones of Daytona, they are only allowed in the T1 Zone (which is on A1A near the hotels-there are only 24 legal short term vacation rentals in Daytona). 

That most likely would be prohibited and disqualify your Ira and you would be penalized as well as paying taxes.  

Is there something in the agreement with the lender that prohibits renting?