While I haven’t gotten anything under contract yet, I’ve managed to land a handful of leads on currently occupied rentals in Detroit proper, Iowa, Indiana and Pennsylvania.

And according to this only 30% of owners can be on such loan, while 50% must be owner occupied.

Most hard money lenders won't loan on an owner-occupied 1-4 unit property.

Does your monthly income assumption of $5,300 account for you occupying one of the units in the property? 

@Tim Jacob, does the 2-unrelated-adults law apply to owner-occupied properties in the county as well?

I'd say that's your biggest risk, btw- with 7 units occupied already, there's bound to be a problem tenant. 

That can be great, but of course you won't be collecting rent on the unit you occupy.

Here is my plan:Jan 2020 - March 2020Buy my first property, located in NC, while I’m stationed in Okinawa, Japan… Read the rest, and please tell me why I should, or should not wait on buying the first propertyThis is what I will be leaving the military with (May 2020):If I don’t buy a property, around $100k ($25k of which is in a Roth IRA) The GI Bill - allows me to go to most public universities for free for 36 months, and provides a monthly housing allowance.July 2020-May 2021I plan on attending trade school for carpentry in the fall/spring semesters.

If you occupy the duplex it will add to the difficulty of finding a private lender as Dodd Frank kicks in, so you wil not find a HML and a note investor may consider it but again the interest rate would be around 12% and over a very short time frame. you would not get a note investor to go longer than 10 years and in this instance possibly even 5. 

The house is currently occupied by the owner.