How would you recommend establishing/building the core 4 in a market outside of where you live? 

A little bit about me thats not related to real estate, I have lived in NWA for 10+ years and I love to call this place home, I am also a sports/adventure photographer sometimes, I love hiking and skiing, and somehow after all these years in Bentonville I am just now getting into mountain biking and I love it! 

If you live near Richmond or have family there, I would consider investing in Richmond.  

Where are they going to live?

Live in one unit, rent the rest.

It will probably not positively cash flow while you are living in it (unless you make some changes that I will get to in a sec) but it would still be a win because you would be paying down a mortgage rather than renting and I imagine your monthly housing cost might end up lower, AND you will now benefit from appreciation.

Purchase price: $275,000 I purchased this property as a live in house hack where I rented out the other rooms to cover my mortgage.

FHA means I would have to live there 2 years and HML payments are higher than I can afford.

If you and your mom want the step dad to be able to live there, have her will it to you and upon her passing, let him stay, rent free or not, unless there is more to it and I'm missing it.

I know with certainty that I would like to live in TN as a result of my travels, and specifically Chattanooga, or Knoxville TN, of which I am currently doing market research.