Thanks in advanceDown payment: ~90k (25% downpayment)Rent per month: 2300 (5Bed, 4 Bath) with 2100sqftProperty management: ~150 (monthly)Outstanding loan around : ~268k (7.675% APR) 30years fixedLandlord Insurance: 1500$ (per year)HOA: 1600$ (per year)Keeping an eye on interest rates for refinance, so I can then move this property to an LLC instead.

Questions they will have is who is the owner, what experience do they have, is their key person insurance against them etc. 

Leave it in your name, get a new insurance policy and call it a day and rent it out

As you alluded to, sometimes a passive note investment purchased for monthly payments “goes south”, and becomes an active participation investment, with plenty of additional capital required for legal fees, forced place insurance, and property taxes.  

Most Florida markets will share some dynamics though like taxes and insurance. 

The biggest form of energy production in Tennessee today, nuclear power, simply wouldn't exist without many, many trillions in tax dollars to develop, not to mention the government stepping up to insure and protect the plants, manage and protect the waste for half an eternity, and clean up the trillion dollar mess in case of another disaster.

Get 3 bids from contractors, get a copy of their insurance etc.- verify the policy is current. 2.

But it's still...whole life insurance.

On top of that, depending on the severity of the structural issues, you will also likely run into problems getting insurance on the property or wind up needing to purchase very expensive insurance. 

If I paid cash for this property, the HOA + Insurance + taxes is around $500 / month.