I've lived in this home for two years now. Roof is probably at least 10-15 years old, perhaps 20 years.
We started noticing some water stains on the ceiling soon after moving in. On a closer look, it seemed like the previous owner painted over prior stains to hide them, so this may have been an issue for a long time. It only seems to worsen when we have a very heavy storm.
Fortunately there is a crawl space close to the issue, but unfortunately I can only see a portion of the area where water is seeping in. The area that looks bad is right where the front of the dormer is (window side).
The other dormers on the roof also seem to have the same moisture issue within the crawl space (though not bad enough to cause issues with the ceiling).
When inspecting the issue from the roof side today, the only obvious issue observed was that J channels on the dormer sides were clogged up with dirt and some moss growth (cleared prior to the picture).
Red area in the image shows where we have definite water issues, orange area is unknown (no crawl space access).
All of the roofing guides I've read show that the dormer flashing should have been done differently. The flat portion should be four inches away from the sides (it's at most 2 inches for ours), and the apron should be covered by shingles on the sides (not on top).
Since they did not follow the regulation on the above items, it also makes me suspect other issues that may exist under the roofing. Perhaps the underlayment does not run along the wall of the dormer.
