In an attempt to add value to her and the education they will be providing me, my thought is to hire a friend of mine who produces high quality video content for real estate agents and auctioneers(yes, there will be drone footage).

A zoning change could be to your advantage. 

I would have the system checked , maybe the filters need to be changed . 

We are not currently living in unit 2 and have not changed our status to homesteading.

I think if you break even today you’d still be a net winner in 5-10 years with higher rents, appreciation, loan pay down etc...most people I talk to can’t change their life with $100/mo cash flow or even $250/mo so if it’s $0-$250 it’s virtually the same.)Are you planning on using property manager?

Also, I am always looking for advice/education on getting creative to acquire anything from 2 units to 20+ units.

Just have him deed the property to you, no money changes hands, you start making the mortgage payments and get the house listed for sale.

Rent to own was a good strategy till 2014 when Dodd frank changed the game and considered it a predatory lending practice .

My mom and siblings both lived in Nashville/Franklin for a few years and I got a chance to see how much change is going on down there. 

About a month ago I really started to educate myself on Real Estate Investing and it didn't take long to find BP.