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Homeowners insurance won't pay anything for a roof if the only "damage" to it per se is that it's old (I.E. wear and tear) which is what to this point has been described here. I would hold out as long as possible for a hail storm, especially if you have replacement cost coverage on your homeowners insurance. A roof can have up to 80% of its granules gone and still shed water just fine. Depending on how much curling is taking place - I would talk to your insurance agent for a recommendation on a roofer(s) and then get multipe bids and opinions as to whether full replacement is really necessary. I wouldn't consider it personally unless leaks were springing up and coming back after attempting repairs.
If you have a 60 SQ roof you are living in a palace.
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