Shane, it is difficult to handle this situation without emotion. I have gone through something very similar in which a property I had just done a full remodel on was completely destroyed and we ended up having to gut it to the studs. It is still vacant to this day as I have been pre-occupied with other investments. I have a property management company in Upstate NY and I would certainly not recommend bringing this up at all in a personal manner. Your investments are business and thus are all interactions that relate to your investments.
We provide our clients with an inspection report upon new tenant placement, then a new inspection every 6 months. These inspection reports are very in-depth and include a full set of photos that document the property condition. These inspection reports are absolutely crucial in determining a judgement in court for damages. It sounds to me that you absolutely need to stop running your investments with your heart and run them with your brain. If we had a tenant that had dogs without prior approval, they would be given 12 days to comply, then we would either begin eviction or request an additional security deposit and a pet fee added to their monthly rent.
If we have a tenant that is responsible for the landscaping of the property and they fail to maintain per their lease; again they are given 12 days to comply and then the eviction process begins, or we send a landscaper to abate the issue and send the bill to the tenant. If you give ANYONE an inch, they will take a mile. We are all in this to reach financial independence and that won't happen by being the nice guy.
In closing, put together your argument for court, sue for damages to the property. You have to go to court prepared, bring in your contractor to testify, have them bring in their estimates, invoices, log books, employee time cards, material lists, receipts, etc. Anything that will prove what you're suing for.