Almost every difficult home insurance conversation in Lee and Collier counties turns out, once you get to the bottom of it, to be a conversation about a roof. Not about the house, not about the claims history. The roof.
Why it dominates
A Florida property carrier is, to a first approximation, in the business of paying for wind damage, and wind damage arrives through the roof. An older covering is more likely to fail, more likely to fail expensively, and more likely to take the interior with it when it does. So roof age is the single variable carriers underwrite hardest on, and several will decline a risk on that basis alone before looking at anything else.
Thresholds vary by carrier and by covering. Shingle is treated more conservatively than tile or metal, which is why two neighbours with roofs of the same age can get very different answers. There is no single statewide rule, and anyone who tells you there is has one carrier in mind.
What helps
Documentation, mostly. A permit or an invoice establishing the year the covering was installed is worth having to hand, because in its absence an underwriter will estimate from the county record and the estimate will not be generous. A wind mitigation inspection on form OIR-B1-1802 records roof deck attachment, roof-to-wall connection and opening protection, and the credits attached to those are real money on a Florida premium.
If a carrier has declined you or non-renewed you on roof age, that is not the end of the conversation. It is the beginning of a different one, about which carriers on our shelf write that age with that covering, and whether the surplus lines market or Citizens is the right place to land while a replacement is planned.