Individuals are purchasing these properties, rehabbing them, and raising rents.

The tenant then decided to vacate the property and leave a mess in the process.

It can accelerates process and can make numbers look very attractive (if you are open to renovations, does not need to be crazy)

We would have preferred to work with them within reason to make it a quicker and easier process.

Quote from @Nick Am: I own a rental property through a single member LLC (say LLC-A) and I am in process of purchasing another property under the same LLC-A.

I explain renters insurance during the tenant selection process.   

I think if you can nail that down you will be able to find a market easier.As a buy and hold investor some of the things that were important to me when deciding on a market were landlord tenant laws, price to rent ratio, housing demand, ability to build a team, large population 500K plus, multi-family availability and some other factors.take the process step by step and you will be fine. 

But the IRS allows this deduction to both of us, due to them taking shortcuts in their auditing process.

Whether you’re a mortgage broker, real estate broker, or running a private lending shop, what software and processes have been game-changers for you?

But consulting with the town would be good to try to understand what they're permitting process is like.