Made me sign up for a re-occurring pest control service at my expense* Got a new refrigerator as old one broke* AC went out few times in summer and they would not wait for home warranty to schedule service.

Seems to be a reoccurring thing in our area.  

I built and sold 3 successful tech companies, was a CTO for two top US firms in DC as well, so let me play Devil's advocate — AppFolio and Buildium both offer reoccurring task/maintenance features for tracking such items like filters, law care, etc., however a simple operations change will fix all these issues.

Normally the company issues a warranty guarantee that the problem will not re-occur

I also needed to set up some reoccurring transactions to by business checking account to keep my fees down so this was actually somewhat timely.

Be very stern and have consequences for reoccurring action that affects the culture of the house negative.

Take everyones advice/lessons and make your opinion as you hear enough/learn the themes that are reoccurring. 

Even self managing all of the other reoccurring costs will leave little NOI left for debt service and profit.  

My preference is if I need 5k per month to live I would like to create a reoccurring revenue stream of 5k and then have $xx lump sum for flexibility.  

In SC it only costs $110 to create an LLC with no annual or reoccurring fees.The benefit of the family trust is that everything it owns avoids probate for my heirs.