Quote from @Jeremy Dugan: I am a US Air Force and Massachusetts Air National Guard veteran with 20-years of experience as a military Civil Engineer.

My family makes a joke about how those items aren't "Nickproof") At this point we decided to call it and come back tomorrow. 

Have them send you a line by line item of what's needed.

For Non-Admitted carriers, the important item to then pay attention to is the AM Best rating (or equivalent rating agency).

If a storm happens immediately after you replace the roof, the actual cash value is the same as replacement cost, so you've lost nothing.The only thing you would have to worry about are items you did not intend to repair

The main issue is that to do the ADU you have to spend so much bringing other items up to code like electrical, plumbing, lighting (windows) and egress.

The complaint has a list of items they are suing for.

Wind is one of the subtle items that Insurance companies are starting to exclude. 

Here is a critical item I ran into with other properties: Avantstay has a vendor to take out and bring in the bins.

Another struggle i have with STR is replacing small items continually which ties back to pricing.