If you haven’t already, make sure you’ve documented everything thoroughly—photos, messages, invoices—and highlight the guest’s negligence, like leaving windows and doors open in extreme weather.If you haven’t heard back after asking to escalate, follow up again and politely but firmly request that a senior claims specialist review the case.

If you are looking at it as an investment, and you hire a PM, be happy if it has a negligible cashflow if you are financing. 

Though we know you are not, an attorney can paint you as negligent and feckless which caused the tenant all kinds of problems.

The best deals I find are usually due to agent negligence of the area and a very poor listing presentation.

They can help you understand your available options and file claims for damages or negligence.

That includes going to the bank and getting a cashiers check.Pay them at the bank, get deed notarized there, then take it to Register of Deeds and file deed.I have done this a half dozen times to keep from missing out on a great deal.For what I'm paying any risk is negligible.  

So, the additional cost to them is more negligible.

The only time you see that is when the landlord is truly negligent. 

If there are clear signs of negligence (kid throws down, paper towels, food, fats) then you can get the invoice from the plumber with the notes and present it to them. 

This will work for ordinary losses, but not from negligence or unlawful activity.