May risk more damage but tenant pool is extremely consistent. 

Some of the boards became damaged on removal, not sure if we will re-rout the edges as needed, or just buy a few replacement boards.

I assume you own this property in your individual name - if you employ a property manager and they make a big enough mistake, you could get sued personally for the full amount of damages (and ignorance of the law is NOT an excuse here - I've seen that one play out). 

But if you are not 100% responsible with your spending or you seem to forget that it’s not your money you will do a lot of damage.

I dropped prices a bit in January and ended up with a college party that did over $3,000 damage and needed substantial additional cleaning.

and be aware that damages frequently occur with that demographic.As others mentioned, 29 Palms Inn gets it right and is about the only successful "destination" hotelier I've seen in the area if you want to market to out-of-town visitors.

You failed to report an issue that damaged my property.

I think I want to evaluate the individual's rental history -- at least regarding property damage, pet problems, etc. -- and I want credit information for the company.

The apartment complex I worked for required all tenants to have a minimum of $100K liability and you'd be surprised at how many times we had to use their policy for some sort of damage to the property (i.e. flooding, fires, etc.).

Based on your story, your credit had always been dinged, so it wouldn't do more damage.