My mom is 60 years old, single, and does not make much money as a private school teacher.

Experience is a hell of a teacher! 

Tough in my region with a relatively short season so looking at options to bump ROI through off season occupancy via corporate tenants, school teachers, etc..

There is no better teacher than experience. 

Realtors are no different than waiters, teachers or cops, etc.

If the VA fails, you have failed as a leader and teacher. 

You sound a lot like the sort of male teacher who would have a closed-door meeting with a too-sexy-for-school teenager in his office, and then, when questioned about it, would act all offended and ask, "What?

But ultimately going out and doing it will be the best teacher.

Working with teachers salary.

Being in another expensive market myself in the Bay Area, house hacking is one of the easier ways to get started and learn the management process (Experience is the best teacher).