Was it just wear & tear or did something damage the roof first (ie. 

I initially felt that I would therefore cover the cost of the windshield to help put but the damage to the frame requires more body work to make the car safe and that would cost at least $2500.

Also do not let the late rent go more than 2 weeks because the entire eviction process can take a month or so and the earlier you start, the less time they have to do some serious damage. 

I was given a suggestion by a contractor to use that to change the damaged roof in one of my flip projects, so that I don't have to put money out of my pocket and it gets carried forward with the property tax for new owner.

Who knows how much damage might be done to the house in the process.  

Landlord/Agent may enter the dwelling unit after providing due notice to the Tenant (24 hours) when the Landlord is required to allow access to the Department of Housing and Community Affairs for an inspection; or when the Landlord has good cause to believe that the Tenant may have damaged the dwelling unit or may be in violation of County, State, or Federal law.

Imagine having to repair a AC unit, water heater or fix damage done by a tenant, all while holding the unit vacant.

A short sale can do some damage to your credit - probably knock it down 200-300 points and will take 7 years to come off your report.

I had one applicant claim that they had no evictions or trouble with any landlords, and found out by talking to the previous landlord that they had left owing money due to unpaid rent, damages to the apartment, and unpaid utilities. 

Keep a copy of the guarantee of the 2 year policy, the original treatment date and the 2nd company's inspection report showing termite damage in the event you have to file for a civil court case.