Our house is about 70 years old.
We have a chimney that only houses the venting for our hot water tank. It runs from the basement up through the roof. Our house is a Cape Cod and the second floor has a cathedral ceiling and the chimney is exposed.
There has been a leak around the chimney for a while now. We had a masonry repair guy come out who installed a new liner and pointed the chimney on his recommendation - the leak got worse. Another guy came out and replaced our entire roof (it was previously shingles nailed to plywood) including the ridge vent and flashed the chimney with metal flashing. We still have a leak. Water comes out the bricks and also runs down the outside of the drywall (so, inside the room).
I need some ideas - we've already spent a ton on guesswork.