It started out through Airbnb and then landed a direct booking.  

"All Diversified Lending LLC" based out of Arizona?

Talk with your tax person or a 1031 Intermediary.  1031 must be land to land. 

There should not be a $100,000 discrepancy in the dwelling coverage (based on a replacement cost estimate.).

There are plenty of renters due to the army base, a management training ground in Juarez, a large number of our employees always to a home to rent, and other factors.

Blue Ridge looks attractive based off my search and pricing there. 

They'll make you rip open the walls to inspect and then reclose them up on your dime.I'd say follow the municipal and lender guidelines as closely as possible for rehabbing, you'll feel better knowing your bases are covered.

I would think it'd be pretty simple to calculate his actual rent income based on the properties current conditions and explain that at best, the tenants in place stay for years to come, he continues doing the bare minimum, and his highest predicted income is x dollars, barring any emergency spending to keep the tenants happy.

@Patrick Philip Keep in mind banks will price there construction debt based on the Fed rate & expect to pay WSJ Prime +1/2 to 1 Point so 10% is not bad from an alternative lender at this time.

I am based in Tampa but I cover from Orlando to Spring Hill, and all the way down to Sarasota.