Since your goal is getting into commercial real estate, it might make sense to start with a smaller rental property like a duplex to get experience managing an investment.

Your account structure depends on your goals for growth and if you plan to self-manage or hire a PM.

Is your house in an area that is appreciating, easy to get good tenants? 

We also offered to help them find new housing, relocate them for free and help in any other way we could.

Also, I put stock in the fact that I can manage things well and that I try to operate above reproach.

Chances are they are paying others who are not as accommodating as you (amazing how people will make those car payments while jeopardizing their homes) - and it's time for them to move on to housing they can afford and to a tenant that does not require you to subsidize them.  

Only because it's $250K for a house?

Rank them from best to worst in management cost*4.

In davidson county most people book an STR to be close to downtown or at least close to somewhere cool as a secondary priority (like 5 points or 12 south for example).If you have an STR in white house it's going to need to make up for location.

Hi Jeff, as everyone has mentioned, I would suggest house-hacking a 2-4 unit if you have the means.