after listening to the podcast my thoughts are that taking that position requires skills regarding calculated risk and slightly different aims regarding exit strategy? 

Parents more safety conscious and it’s as much a negative as a draw.Smaller families (rarely more than 2 kids) so bathrooms better than the extra 5th bedroom...once you get past maybe 2300square feet it’s wasted spaceThe parents of 30 year olds are the last generation that grew up watching their parents fix and DIY those skills are rapidly declining.

There are going to be issues between the tenants, but if you have a PM company or good conflict resolution skills then you'll be fine.  

We are both beyond new to this entire thing, but collectively we both possess skills that could make this pretty streamlined and profitable.

My skills set is probably better suited for Appraiser, however I am open to learn sales or whatever is needed.

It's just a matter of deciding the correct path for you depending on your skill and the amount of time you can commit to real estate. 

I’d rather spend my time learning a new skill that will save you time and money.

With the landlord/tenant environment in Virginia now, tenant screening is a critical skill for any landlord/property manager.  

More importantly, your long-term renter has no training, no known skills, no supervision, and no incentive to perform well.Sorry to hear about your troubles.

Although I am planning to continue working within Education as well, it has become glaringly clear to me that rental property investing may be the best tool/skill around that can help me achieve financial freedom.