SolarAndWood said:How was it flashed originally? Is it still there? Can it be reused and just reinforced with his step flashing and caulk? This is a major weak point in a lot of roofs. I don't think I have ever taken one apart and not found rot around the chimneys. I don't think I would rely on caulk to seal the step flashing to the masonry.
I can't tell exactly how it was originally flashed since it is all slathered up with caulk. The step flashing only gets nailed down to the roof. The flashing that covers the step flashing gets sunk into the mortar joint. I've read that it should be sunk into new mortar on one website and into caulk on other websites. I think either are fine I guess.
The contractor said the flashing will be all new. And yes, my rafters near the chimney have some rot which I need to reinforce.