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.

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

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

If I donated to aids health foundation and they spent the money on rent control instead of aids research or health care, I would be pissed.  

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.  

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

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