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.

Live below your needs on the interest generated from $2.4M in the stock market.

I occasionally enjoy co-hosting (splitting costs) for client events with a lending partner but that is pretty rare as most lenders just want to hold "first time home buyer" classes/events or co-brand online ads for home buyers.  

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.