With a few chimneys over the years, that have needed work, and having paid $$$$ for professionals llto repair, repoint and seal, only for the problem to persist or re-appear within a couple
Does the end of the house where the chimney is face South? If so, it is possible that the wind driven rain is saturating and penetrating the brick. We had this problem until we had water seal applied to the chimney bricks. Our fireplace is brick and the face was wet and there was dripping water inside the firewood box.
There is a device called a Rilem Tube which would be placed against the exterior of the chimney and would simulate wind driven rain.
years, due to shoddy work ... I can relate and sympathize. This fall I decided to redo the top of our one chimney myself, to a much higher standard.
I would start by looking at the very top, or having it reviewed by a chimney sweep, rather than a mason.
Is there a cricket ( raised roof section ^ ) behind the chimney if it meets a slanted roof part, to divert water around the chimney?
I don't know why some designers and architects skip including crickets ... and will put flat walls in front of sloping roofs. If there is no cricket, you may need a contractor to add one.
Is there a cap on top of the flue?
Without a cap, water will enter the chimney and will then find its way gradually through the interior aspects of the chimney, along ledges, looking for protrusions and gaps.
Beyond that, there could be gaps in the very top, perhaps around the flue tile. Perhaps between the chimney and a wall face.