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

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

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.

Non-passive to achieve this level of return.Add the addition of the ADU makes the main unit rent controlled if over 15 years old.the work to add an ADU likely exceeds the effort of a brrrr that can achieve infinite return  Experienced investors are adding multiple ADUs by leveraging items like bonus density, committing units to affordable housing, etc.  

The best place to start is with a spreadsheet that has every every cost itemized. 

We have 8 business entities availing of their services, and as "advisors", they should make business life easier -- not add more work on your plate --- but instead, my team and I have been checking for mistakes, or following up on action items, missed deadlines, and paying penalties to the IRS and Secretaries of State due to their negligence.