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.

Do you think that is beyond the skill set of any competent CPA?

It’s an invaluable skill even with all the calculators that exist out there.

How do I get started, how do I learn this skill?

Perhaps people skills are not in my DNA or should I start reading Dale Carnegie?

To do a good job selling houses you need a lot of persistence and organizational skills.