I recently bought a 90 year old house that had roof leaks around the chimney, and evidence of many years of water issues in the area. I already had the chimney replaced above the roofline, a new chimney flashing, and new roofing put on. The leak persists despite several attempts by the contractors to fix it. The chimney/flashing guy will be back again next week to give it a 4th try.
The main problem is the location of the chimney. One corner of the chimney is right up against one hip of the roof . . . snug against the hip rafter. The flashing can't go up much and the cap shingles can't go down much. The previous owner "solved" the problem by encasing the entire area under about an inch of tar.
Is there a really slick and professional way to deal with this problem . . . some clever flashing configuration that doesn't involve gobs of sealant? Help please!