Below is some copy & paste info about our methodology:----------------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

I'm going to try leasing the place out myself again, but if I'm struggling, I will hire property manager. 

After years of self-managing our single-family rentals, we decided to hire a property manager to provide full service management.

We also require that we be added to the contractor's insurance as Additionally Insured, so we're covered if they cause damage or liability issue.3) If the property is occupied:- One of our people MUST accompany their person (and we charge for this). --- We were sued many years ago, along with the owner, because tenant claimed owner's contractor sexually assaulted them!

This is our boilerplate language:Insurance: Tenant should obtain a renters’ policy of insurance on their personal property.

Can you point me to a reported decision where a court ordered money damages in lieu of specific performance when real property was the subject of the dispute?

Give her 30 days notice now, keep her security deposit, and send her a additional bill for damages to the unit in lieu of taking her to court for the damages.  

The guests have a credit card on file and your policy should allow you to charge for damages or excessive cleaning.

In July of last year a roof leak developed and caused damage to the ceiling in my unit, to the point there was partial ceiling collapse. 

Quote from @Brendan Jones: For the homes, and or properties that you will use as a primary or a rental property one big thing I look for is infrastructure in the area, extrinsic value (I.e. hospitals in the area, schools, and job market), and the last thing is creature comforts for people (I.e. is a store to get groceries 1 hour away or 2 minutes away).