I don't think the insurance is very expensive.  

what is damage protection insurance? 

Good insurance, particularly with an umbrella liability policy provides very adequate protection on smaller assets. 

Include an exit strategy, tax planning, and insurance to protect both parties.

I've only ever purchased homes as primaries, one being rented out currently to an insurance company and the other is my current primary.

Does anyone have a set of questions or things they think through or scripts or anything that helps them approach, talk to, and close on deals with homeowners when they approach them directly (whether through mass marketing, driving for dollars, or otherwise)?

One thing you may want to consider is some sort of umbrella insurance - that might be a cheaper option, I'd price out bother.

If I keep the house in my name and use it as a rental, would I need to do anything other than notify the lender and adjust my homeowners insurance to reflect the house is a rental? 

The county discovered I was renting out my home and property taxes more than doubled (lost homeowner and two other exemptions).  

You should also check to ensure they have Errors & Omissions insurance, Fidelity Bond coverage, and a Financial Institution Blanket Bond.Some are more consultative and advisory and provide guidance, while others are just processors.