They cover articles related to new businesses/developments in the NKY River Cities. 

I'm charging $1,500 to $2,000 right now, thinking it should cover normal wear and tear and minor damages.

You simultaneously have an Option to purchase your house back for 1.1 million and you have a lease that you will pay to your new landlord which will cover all their expenses.

My typical investment in Colorado has been around a ~500k purchase price, and I really strive to purchase property that is $20,000 to $25,000 under market value and that is break even cash flow minimum after operating expense/debt. 

A lawsuit can be filed in the future for a problem that happened when you had no insurance which is why your lender wants that gap covered.

Explaining those cover there *** clauses to save there scamming hides! 

@Ray Williams E&O doesn't cover slip & fall liability issues at YOUR rental.Doubt their commercial policy covers anything but slip & falls at THEIR office.So, they should want you to add them as additionally insured, so your insurance covers them for a slip & fall at YOUR rental.

IE> If there is an issue and someone gets hurt you can be sued if you don't have insurance or if theirs does not cover you. 

From there I can typically get an idea if we even need to go any further. 

I would exceed the minimum requirements on this.Get a standard STR policy and make sure the pool is specifically mentioned and covered in the policy.Then you can look into an umbrella policy.