So I crawled up into the attic and the plywood butting up right against the chimney along one of sides has slight water damage/rot so it deffinately is just leaking around the very edge. I also went on the roof but there was nothing much to see up there... The flashing looks old but no obvious entry points besides some cracking dried out tar looking stuff pretty much all around the edges of the metal where it meets the brick and the shingles.