We built a new house 3100sqft, 4 Bed, 2 ½ bath for $310,000.

From there it's up to you on selling. 8 years you should be not breaking even unless this place is in a rough area or needed a ton for repairs over the years.

If the property does not require an extensive rehab and just needs cosmetic repairs then a standard landlord dwelling policy in most cases depending on the carrier.

Stock market returns have been good and I don’t have the headaches of dealing with any additional houses or guests.

This is very useful.You could build a deck or gazebo to house a hot tub.

In previous roles, I was responsible for the asset management, capital improvement, repair, and maintenance of an ANG Fighter Base worth over $400M.

I hope this house eventually stabilizes. 

A more realistic expectation is 24 hours which will ensure we can arrange any repairs or corrections with a team, handle it in person, etc. be curious how this plays out as I worked for local developer for a while and developed several properties in Alexandria (Specifically old town) and while the city is challenging like any city - they were mostly realistic.

It's also rare you buy these properties with 20-25% and have NOTHING you need to address almost immediately in terms of repairs or capex. 

Even with the mortgage paid off, some of the $2000 in rent will go to maintenance, repairs and property taxes.