You should work with a CPA or tax professional that can help you with structuring your business properly first. 

Create a short, professional explanation of proper/improper use.

I am going to install quickset locks and they are all metered separately but looking for functional tips during the rehab process that might make our lives easier in the future and management tips.

If all necessary notices have been properly issued, the property owner should definitely proceed with filing for eviction.

I have Proper insurance, tailored to short term rentals. 

They provide great education on how to properly buy and manage rent property and they have a huge physical office in your backyard.

But looking back, I can’t help but wonder why my agent didn’t advocate to ensure the property was clear for a proper inspection.

A huge key to a good relationship with your PM is vetting them properly, like you mentioned.

A secure building will appeal more to potential tenants and provide peace of mind.Energy Efficiency:Ensure the property is energy-efficient with proper insulation, energy-efficient windows, and appliances.

(Trying to skimp on coverage by not telling them you're Airbnb-ing the place will defeat the purpose of insurance if they deny a claim because you weren't truthful.)There are specific STR insurance carriers like Proper Insurance, but most major carriers offer a rider for vacation rental or short-term rental insurance as well.