@Alex Bacon there are 7 different insurance carriers I use for my OH investors. 

The financials are as follows: Purchase Cost:  $247,000Cash Down: $37,000 (15% Down) + $2,500 (closing) $39,500Mortgage + Tax + Insurance: $1,548Monthly Rent: $2,250The house already had tenants who were signed on for the next year we closed July 25th, their new lease started July 30th and runs through the same date 2019. 

That is simple not that case and that is probably why the first property is usually the most expensive to flip because you learn those things.When choosing a new contractor, i ask other investors or realtors for references and i make sure the contractor is licensed and insured.

We tell her to file with renters insurance, which is strongly encouraged by lease but not required.

What paperwork do I need to insure that he pays me back?

You would be putting it under your personal name, but the rates would be more like 5% and make sure you have the proper insurance in place. 

However, I have been an insurance adjuster for 15 years, I have replacement cost on ALL my properties, both personal and investment. 

However, I don’t really want to sell to an investor, though I would avoid all the fix costs and all of the maintenance (termite contract, lawn fertilization, a/c maintenance contract) + taxes and insurance for the next 14 months.

Now there are problems and you will need to protect yourself and a good insurance person is needed too.

If you decide to go forward, make sure you get a really good person to review the title and get title insurance.