Using a small broom or brush sweep the roof near the skylight.
How to re roof around skylight.
If the skylight is installed on a low slope roof the curb should be even taller to allow for 8 inches of flashing.
Install from the bottom up lapping each piece on top of the lower one.
A journeyman quality roofer would should be able to flash any part of a roof the requires flashing.
If you have to replace shingles around a skylight examine the old flashing.
If the skylight is in good shape then no reason to replace.
However if you use high quality thermal glass for your skylight you will likely not run into these issues.
Unless the mortar and bricks were in bad shape.
Since the skylight is positioned on the roof it can cause some energy related issues in comparison to a regular window.
The national roofing contractors association recommends using curbs that are tall enough to allow for a minimum of 4 inches of vertical flashing on all sides.
There is the potential that the skylight can lose some heat in the winter and bring in more heat in the summer.
Install 6 in wide strips of a self sticking waterproof underlayment.
How to roof around a curb mount skylight.
Gently look under each shingle and sweep away any debris.
You wouldn t replace a chimney you simply install the flashing properly.