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

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.

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

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.

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.

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.

Live in one unit, rent the rest.

I was going to continue living with my parents until the renovations were completed.I hired contractor 4, put a lock box on the property and starting purchasing materials and placing them in the garage for the contractor to get started.

We should be able to rent each side for $1800, but looking at living there for a year before we find a long term primary residence.

My hope with house hacking was always that I would be able to buy a multi-family property, live in it for a few years, and then move to my own home while hanging on to and renting the multi-family.