He thinks it was all a lack of experience in doing a title policy on something like this? 

I think the biggest Pros of not finishing college currently are the time and freedom I have (no obligations to family or spouse) along with the resources I have available, the biggest con is obviously the lack of a backup plan.

They make a ton of money because they rarely pay out either because a lack of claims, a lack of qualified claims, or straight-up denial of claims.

I would ideally like take advantage of my VA Home Loan and House hack a multi family although I know the DMV area lacks them.

just find someone who has done what you'd like to do and offer that person something they are lacking, whatever that might be. 

Typically for someone our age and who lacks experience, it would be highly unadvisable to start with something like commercial real estate, or even wholesaling. 

@Michael Odugbesan That's absolutely true but I don't bother mentioning it because lack of honesty negates every other quality.

You should probably reconsider having him serve in that capacity based on his clear lack of good judgment, or at the very least make him read the landlord-tenant handbook front to back, especially the part about a tenant's right to privacy and the part that states: "any uninvited sexual advance, solicitation, request, or demand for sexual compliance is considered harassment" (at least that's what it says in the handbook for my county and I'm sure something similar appears in most if not all).

Many people that go 'fishing' in real estate lose every penny they own because they lack RE education and insight. 

When I call on a public request, the other person's responses or lack of interest in my questions will determine my attitude in wanting to complete their request.