They need a place to sleep, cook, eat, take a bath, do laundry and have a good time drinking beer.My renters are sort of like your renters. 

Short term (to ins co) means partying and drinking and much more liability, so yes please have good coverage and make sure they know how it is being used!

Luckily, I was a project manager in a past life so I already have some of the skills needed, but I have been drinking through a firehose learning how to do this well. 

I often break it down into the "five pillars" of protecting your assets.1st pillar is avoiding unnecessary and risky activities (don't drink and drive, insurance generally won’t cover your poor decisions) and take good care of your investments - these simple steps will help you prevent lawsuits before they even occur.2nd pillar is a good insurance policy as that cover the majority of your exposure.

But over time, people kept spilling drinks on the pool table, bachelor and bachelorette parties kept booking my place. 

But having to walk away from a table full of food and drink occasionally, is a tough one. 

Meet the tenant, interview them, see who tags along, did he/she respect the appointment time, did the park appropriately/respectful to neighbors, did they smell of smoke/alcohol/etc.2. 

We always leave water and soft drinks in the refrigerator with a sign telling everyone to help their self.We always leave plenty of toilet paper since for some strange reason the very first thing many prospects request is the location for the bathrooms.

Why don't the 3 of us meet up for some drinks/coffee and do an informal one?

If I am ever in Maryland, I would definitely love to grab a drink and pick your brain!