Our STR/MTR portfolio typically sees around 80% occupancy, and I’ve noticed that the online travel booking sites often push properties with consistently great guest experiences.

Typically a new roof only makes sense to protect the asset.

That is very typical of the "advice" I see given by the students in his group.

Midwest cities with populations under 300,000 typically have cheap property taxes.

Would you think changing my minimum stay on Airbnb would be worth it?

Not worth the hassle/risk to claim.

The intricacies tax planning with a rental are worth hiring a professional, even if you just do it once for an overview. 

Quote from @Jonathan Blanco: Is it worth seeking lenders with $0 lender fees (such as origination, processing and underwriting fees) or do they just get that money by increasing rates and charging higher points?

Myers, Net Worth, New Western, Homewood, they wouldn't be as big as they are if no one ever had good experiences with them.

It's absolutely worth it.