It tracks all maintenance requests well and you can make notes, add pictures, videos and communicate directly with the tenant in the maintenance request.

Where are they going to live?

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.

I would try am accommodate as much as possible since they have to take days off work.You could do a video walk through to document everything or do it while the cleaners are there.I don't do a post walk with tenant and the new tenant agrees everything is in good condition when they sign the lease.Try and be flexible.

Live in one unit, rent the rest.