Having too many will cause for overlapping of properties and then it goes to procuring cause in which one gets paid. 

It’s not a binary cause.

This is a good tenant of 5+ years, and I don’t want to cause unnecessary friction (I’m just trying to set up automatic systems for myself).

In my experience tenants on the lower end of rent tend to cause more damage than higher price tenants.

A variety of things could have caused this.That said, what you've described above is not so untypical in terms of the steps of the process for a fix and flip loan.  

So it's important to ensure you have records and the issue is that sometimes guests go in with lotions etc. which cause irritation. 

Most likely the state where the property is located is where lawsuits would be brought if they are something for personal injury like a trip and fall or something of that nature because the “cause of action” arose in that state.

Chicagoland as a market may appreciate at different rates, and property taxes certainly do not help the cause.

The plumber determined that the issue was caused by someone driving over the cleanout, breaking the pipe.

You could also add a clause about your ability to terminate the lease if they cause problems in the neighborhood, don't cut the grass, etc.