I would have the insurance oney replace the siding ADD INSULATION! and try to have the roof replaced at that time too.
You might check with your states insurance commision, if all the other same age homes were approved for roof damage, the insurance commision MIGHT be able to get yours approved too.
do you have replacement insurance? or depreciated insurance?
replacement insurance costs more but whatever loss gets you a BRAND NEW whatever
depreciated cheap insurance works as follows:(
the 30 year old roof is damaged. a new roof is 10 grand. Divide 10 grand by 30 years, unlucky you heres your check foir 250 bucks have a nice day, you are paid in full.
look if insurance wouldnt cover it you still needed a new roof its 30 years old:(
Its cheaper to replace NOW before roof leaks damage rof deck and bring down interior cielings and cause mold!