I also noted damage to the gutter at the side of the house at the driveway.

Going forward, this can be a huge issue for more extensive damage. 

I flip fire-damaged properties and own a restoration company which specializes in fire damage.

Dents in drywall from doors or furniture, large or numerous holes, heavy staining or obvious impact damage fall into tenant-caused damage and can usually be charged.

Courts tend to look more favorably on charges that are specific, documented, and not structured like penalties or double recovery.Separate rent, damages, and admin costs.

Make sure you have an iron clad agreement that pet damage will be deducted from their security deposit or, for Airbnb, I let them know that all pet damage should be fixed or reported and paid for before checkout, or the guest will get a negative review.

I feel terrible for his family, I cannot even imagine the psychological damage and eventual financial damage, and possibly even criminal damage so many of them will face as a result of his wrong doings.  

Its not necessarily damaged.

Quote from @Giovanni Choisne: With the recent severe weather and other unexpected issues that can come up during a project, I’ve been thinking more about how experienced investors factor in the things you can’t always see upfront.Even when the numbers look solid, surprises like weather damage, delays, or hidden repairs can change the outcome quickly.

Not doing those can lead to water damage and further issues.