Ensure the state provides a clear title upon sale.

I will be managing and will be paying a real estate agent friend to show the properties for me.

You also need to consider that at a lower percentage of money down you will be paying a Mortgage Insurance Premium or MIP. 

You really don't need that LLC until you pay off the property and it's questionable if you need it then as long as you maintain your property and have correct insurance.Yes to wind insurance, not sure about hurricane.I use Foremost STR policy for one property.I am about to switch to USAA (retired Navy) for another because they quoted a policy that was 3k lower than what we have.

Most businesses, property management or not, fail due to the lack of sales, not due to the lack of systems and phone etiquette.

After diligent searching there are ZERO duplexes for sale within an hours drive of my work place.

SFR houses will only appraise based on comps.So unless someone was paying cash you can't get more than they appraise for.The camp ground is a different story.

Reporting the proceeds you pay to seller on a 1099 sounds reasonable.

Well, how much is the lot for sale for?

You let it slide, waive the late fee, and she pays by the 10th.