Insurers have become extremely conservative over the last year.

Also make sure they have proper license and insurance and name you as additional insured for liability.

Pretty much any way I can add value I will do it even if its a 50k house that will require that I put in hours and hours of work because investor clients are typically return customers. 

I’m aware that money is likely going to be spent but, assuming it doesn’t, then can you still make tax free cash flow simply off of the recurring deductions like interest, management, hoa, utilities, taxes, insurance and depreciation? 

$30k in equity and 100% cash flow besides taxes and insurance.

Or if my landlord homeowners insurance policy will cover this?

After the 2 hurricanes maybe only 25% were still on the beach, but the hurricanes were a pain and resulted in our insurance going up significantly. 

However, depending on your loan type, if you put less than 20% down, you may have PMI (private mortgage insurance) which will make your monthly payment higher by up to a couple hundred dollars.

So, investing in a market you don't know is like saying: I am going to open a retail business without knowing what product you will sell, how to source the product, or who your customer is and what drives them to purchase.  

Call the customer retention department at a credit card company you already have a credit card with.