Had he simply paid me the 95K he owed me my company and my insurance would have taken good care of him.

What about property insurance?

After all costs (tax, assoc dues, insurance) we have a positive cash flow of $940.00/mnth. 

However, you must have a relationship with that Non-profit.Flipping Property: Have a friend or a person in line firsts that is looking to buy investment property.This could be your insurance agent, the neighbor up the street that own investment property.

The properties I am looking at will cash flow a teeny bit, enough to cover mortgage, interest, insurance, and 20-30% for repairs and vacancy.

I mean I am turnkey I was the number 24 new home builder out of the top 30 in the Portland market.. and all of are product are TURNkey I suspect  they are brand new homes.. just like the buys I fund here in the PDX metro area they are flippers.. they just NEVER sell to investors its all home owners.. and homeowners want fresh new modern rehab.. so investors same thing they want fresh new rehabbed rentals.. and if you can bring the management component that helps them.. but I bet Memphis has their share of flippers that sell to home owners.. they are turn key in a sense..

The inability to turn over a unit if cleaner is not available on one dayThe insurance/liability aspect (all insurance companies asking if I will be doing STRs) When electronic deadbolts dying before guests show up etcReplacing damaged furniture during turnover (who do you compensate to handle that?)

You know, like the hundreds of thousands of people in the Carolinas who had no flood insurance and who have had their homes damaged or destroyed by hurricane Florence?

Between the annual reports and filing fees, and also the overhead necessary to maintain separation of assets so the corporate veil isn't pierced, the cost-benefit just might not be there.Might make the most financial sense (and most streamlined) to run her as a sole proprietor (Sch C) and carry appropriate and adequate insurance, which you should be doing anyway with an LLC. 

Most renters will not pay renter's insurance and that is a choice but how would they like not to have a choice about carrying insurance because of the potential liabilities and expense should you come up against someone like them ?