Worst Case Scenario in Hurricane - Home

[Steven Segal]

I am looking at insurance on a huge block of homes. The alternative to being insured is going uninsured. 

The question becomes, what is the worst case scenario if a strong hurricane hits Florida...

1. Would the roof blow off? That would probably bring the most damage. You would obviously need a roof and all the rain would flood the inside - it would be a mess. Is there a year when roofs/homes started to be engineered so that this wouldn't happen?

2. The other big issues I see are landscaping, lanai cages, and non-impact windows. 

Any comments on this? or additional info/thoughts I am missing?