Fortunately, we are living rent free right now at our parents but this is becoming a major pain for us.   

It’s a pain to add the bill each month, and then explain how the billing is a month behind, etc.

I like to phrase it as “do you have any real estate plans in the near future” or find a point of pain for them like “I’ve owned this place for 20 years and I’m sick and tired of being a landlord”) It also depends on how close to the city you’d like to be.

Owner still has a standing loan, property has been rented out for the last 7 years and it was last updated around 20 years ago, property was last listed in 2011.Just knowing how the different towns in Rockland work I know that the Clarkstown municipality is a pain so I want to do as much right as I can.

I am curious to hear about your biggest growing pain as you grew your portfolio over time.  

Smart TV - TCL Roku TVs, inexpensive, good quality and dead simple to useSecurity - I have Ring floodlight cameras, I take hard-wire it to wherever an existing exterior light is (and then hardwire that switch so it can't be turned off)Smart lock - I use RemoteLock 5i, I like all their features though the interface is a bit of a pain.  

But right now you have a rapidly depreciating wonder to sit in 5% of your time that's eating up a serious bite of your income. you might as well be throwing a hundred dollar bill out the window every three trips in it.I speak from extremely painful experience. 

Heavy as hell, crumbles, and a royal pain to pull up of they did it right.

This could be an indication that they are going to be a pain from day 1, or it could be an indication that they are responsible tenants who started looking early and found a place they really like and will take care of. 

Do they really do what they promise to do or it is painful?