I blame it on them being upset paying late fees for last month's rent.Advice on how to communicate with tenant in situation like this to prevent them becoming aggressive and what do you think warrants reimbursement?

The way to beat this is by the 5 P's of the Marines: Prior Planning Prevents Poor Performance.

You can also try adding Biggerpockets.com to your contacts list, it helps in preventing the email from going to the spam folder. 

The way I look at it, an ounce of prevention is worth a pound of cure holds true in the majority of cases especially when it comes to maintaining a commercial property.

The are strict license requirements in my industry too (home inspections) but that doesn’t prevent a non-inspector from owning and controlling a home inspection business. 

This will prevent headaches down the road.  

We try to stay preventive with this sort of thing...upgrade to aerator...and ensure the leach field is up to par when purchasing...this is a good example of how bad things can get without proper due diligence and maintenance.

I tend to move fast and take massive action to prevent myself from getting into analysis paralysis, self doubt, or boredom.

You will at least have a judgement against them and while you may never see the $5k again, at least it will go on their credit and possibly prevent them from doing it to the next person.  

This would also prevent people from going in other guest's rooms.