If your home is an older home, circa 1920-1930 or older, you may have and he may have observed that you have the spaced board decking, also known as, Skip Sheathing, which is Plank Boards installed with an approximate 1" to 2" gap in between each board, prior to a Cedar Shingle Roof having been installed as the first and bottom-most layer of roofing, with a minimum of one additional layer of asphalt shingles installed on top of that Cedar Layer.
Rather than guess, you should contact the roofing estimator who examined your home and roof and ask him the particular questions and don't settle for anything less than straight truthful and comprehensive answers.
If the decking is old plywood sheathing, possibly when he walked on the roof surface, he noted a crunchy feeling, indicating that the existing decking was delaminating from either moisture and/or a lack of properly Balanced Intake And Exhaust Ventilation being present and if so, he should have included the modifications necessary to upgrade that to more than minimum standards.
How detailed was his proposal and did he take the time to sit down with you and explain all of the details and point out the features that he included and why?
If not, have him do that and also call around for another Roofers Opinion, rather than a neighbors opinion, who probably does not really know that much about long term roofing problems.
Ed
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