Given your background in bookkeeping and real estate, you likely have a good sense of your capacity and risk tolerance, but consulting a legal professional might still be a good idea.

I never had the choice to join the military or the police/fire dept. in a First Responder capacity. 

It requires more work, so you need to determine your capacity in the end. 

You could, for instance, buy a rental property and employ property management firm to take care of it, but you can't work for your company in any capacity and get paid for it.

I’ve been able to mostly retire from the W-2, I’m still on the payroll there in a limited part time capacity.

David is not a PM, he is a handy man and it was in that capacity that he went to that property.

All wishful thinking aside, please cite specific codes, laws and regulations, MD or Federal, which state that when I approach home sellers in my capacity as a business owner (not REA or Broker) I owe them fiduciary duty and that I MUST serve their interests above all.

Does anyone have an attorney/ title company they can recommend that works with investors in this capacity?

How do I construct my time horizon and my risk capacity?

If you care about this societal issue you will be better served doing whatever that activity that is outside of your capacity as a landlord.