At what point is it time to cut ties with your Property Management Company?
I would say if you do not trust them and your asking this question it is time.. You do business with a company or person as long as your business model matches theirs and your goals are aligned. If you can not say that is the case then it is time to part ways in my opinion. It may be a mutual seperation or they may not care. But you owe to your own properties and your own investments to make the tough decisions
As a property management company owner, I would say as soon as you bring your issues to the manager/owner and they refuse to acknowledge and correct the issues. if they don't value your business, some other company will. Just be sure you protect your interests by reading over your management agreement to ensure you aren't hit with any surprises. Also, interview other companies now, so that you have your Plan B in place ahead of time.
Best of luck to you!