Both properties are under property managers.

We have 2 LLC's that run management companies and 10 LLC's that do real estate investing.

While insurance has covered some costs, the process has been stressful, even with a property manager (their responsiveness to these issues has been slow).

I managed a budies house in a strict HOA and he was continuously being sent bills for fines from things like parking on street or leaving trash cans on the street after trash day.I personally will never buy an investment property where there is an HOA.

In fact, we ended up paying a bookkeeper $450/month plus the $90 subscription to QB online to manage our relatively small portfolio.

I've had a previous life as a loan officer and an inside account manager for a lender.

I am considering putting them under a property manager. 

Outline a business plan, put up investment criteria, creating financial system and invent property management practices.

Gave that list to her property manager in March this year & he just smirk at me.

Because of the debt payoff increase and the cost to furnish (~20K), my CoC is just 5% now (this is if I keep a management fee of 10%, though I'll be managing the property myself).