They ended up having to cancel their project and decided to sell as is because the association required a lot from an insurance standpoint from the contractors, therefore, my client struggled to find a contractor with sufficient insurance coverage for the association to accept.

Wouldn’t supplemental insurance cover anything else that Airbnb’s insurance doesn’t cover?

1) Have them get a liability policy with the landlord as additional insured and proof of coverage, and proof that the dog is covered. 

It will need to provide coverage for the existing structure and what is being added.  

Are you looking to create financial freedom on investing, or is this just a supplement to a holistic retirement strategy?

During 2009 when I bought my condo in SF, to supplement my vacation income, I signed up with a company called Air BnB to rent out my place when I was gone.  

Last I heard, they were second highest in the country, with Miami being #1.If you have a loan on your property, your lender will typically require you to carry "Named Storm Coverage" (NSC) insurance. 

I supplement the costs of all these repairs with my day-job salary, otherwise this would all be over a long time ago.

Obviously the Replacement Cost coverage will bump up the premium but not to that extent. 

One part of their coverage is loss of rents in the event of tenant displacement.