This morning I've been in a creepy place under the roof of the house above the downstairs bedroom. You enter this place through a secret hole in the upstairs bedroom closet, which I created with sledge hammer like techniques in order to do some rewiring. You have to balance on ceiling joists, else your foot will end up sticking through the ceiling downstairs, and those are buried under piles of old fashioned thrown in insulation.
Please excuse dust and old wasp nests. Don't get around to cleaning it much.
There are two reasons for getting in there. One is to scout out how much trouble it would be to rebuild the closet. This is the back side. Obviously just a quick job someone did long ago by putting up some slabs of plaster board. It looks like they removed a roof brace to do it.

It should be diagonal at right angles against the roof.
The other is to try to track down a leak that showed up on the downstairs bedroom ceiling after hurricane Irma. In the morning when I woke up after she came through I could hear a drip, drip, drip on the ceiling, and should have run up there immediately, but was preoccupied with checking on the goats and coping with the power outage. The drip is at least a clue. This leak showed up once before long ago, and I always assumed it was from around the chimney, because it only happened when the wind came from the east (very rare here).
This is looking up alongside the chimney to the attic space. No evidence of water on it. The wet spot is about a foot away from the chimney.
This is looking down a hole, made because two of the 3 fireplaces in the house are set at an angle. I don't know why I'm posting this picture, but it would not be a good idea to drop the phone down there, or to stoop over and fall in head first.
Right now I'm puzzled, but I like puzzles. The best I can figure the water is running down a rafter, *then* dripping down, so it could still be from the chimney. I need to get up to see near the top of the chimney. Tried taking a picture, then zooming, but it isn't clear enough. I really need to get a ladder in there. Yikes!!!