Kevin summed it up simply on-site:
A cedar shake replacement and a typical asphalt shingle replacement are completely different products.
Asphalt shingles are manufactured roofing products. Cedar shakes are wood. That changes the way the roof is removed, the way the new roof is installed, and the way the crew thinks through the details.
With cedar, there is more individual material to handle. There are more joints across the roof surface. There are more areas where water management and airflow need to be thought through carefully.
That does not mean asphalt roofing is simple. It means cedar has its own set of rules.
And if you treat cedar like asphalt, you are asking a natural wood roof to perform like something it is not.
That is where things can get expensive later.

