For residential rental property the tax law is clear. A new roof would be added as a new asset in the year it is complete. It will use the same 27.5 year recovery method as the original rental house uses but of course with a new date placed in service. See the information in the link below for a casualty loss.
The insurance companies may have their specific rules for insurance, however, the tax law is not changed. If your roof is destroyed before the 27.5 year recovery period, then in that year you would use the casualty loss portion of the tax law to deduct the remaining balance. See the link below for more information and steps to entry.
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