You can throw that $550k into an annuity (or similar) and get a decent (and very safe) return.

I likely would take a safe approach in my underwriting and value it with the quads then subtract 15% off the total.  

And if it were set up where everything went through a title company so the buyer pays the title company, they manage the buyer's loan (from me), and the title company ensures my mortgage is paid without my direct involvement... what parts of the transaction would feel risky or not worth the headache to you? 

it ignores (1) all the costs that have to be expended simply to process a transaction, and (2) the higher maintenance costs you will be incurring in that type of neighborhood. 

The IRS views this as a related-party transaction, and deductions like rent paid to yourself wouldn’t qualify.

Processes have been set up to provide a degree of protection to parties  involved in subject to transactions.  

That $2M would be worth $100K on a safe 5% withdrawal rate at that time.

., your tenant stops paying, you're still in a relatively safe position.

Financing must be through non-recourse loans, and you must avoid prohibited transactions, such as personal use or self-dealing.

Especially if they profit from the transaction.