We've always been shy of real estate investments beyond normal home-ownership because we don't know how to make them work, and we've seen more examples than not of people failing (sadly).

If it fails, property taxes will be out of control in the years to come.

What if I approve their application and they fail to sign the lease?

If I don't take this opportunity, I might regret it forever, even more so than if I take it and fail. 

When a tenant receives a legal notice to leave a property and fails to do so, and the matter ends up in court, it's serious.

If the tenant continued to report it but the PM failed to respond, then the PM may be liable.

I had some guy rent a room in my house and he failed to mention he worked nights - I quickly realized this when he'd arrived home at 5 AM making too much noise. 

How I have it set up it allows my tenants to know my expectations and they know to communicate with me if there is any issues with them paying on time and then that is communicated and if they fail they get a 3 day at that time.  

If everything else fails, you can mail them a burner phone with your number..As far as funding family money will probably be your first choice for both the purchase and the rehab.

If they fail to respond/pay, I hand it over to a collection agency.