Below is what our roofing expert John Stout from Go Roof Tune Up
had to say in response to your question:
Trevor in Minnesota,
We received your question and have examined your photos. All of the photos indicate a flashing deficiency. Without the ability to see how the flashing is installed, it is necessary to use a roofer tool to verify if flashing exists. Roofers use this special tool called a solid investigative probe (an old screwdriver) to verify the existing flashing. Having the right tools is why the roofer can charge an “arm and a leg.”
One of the photos shows counter flashing. Your probe will show if flashing exists behind the counter flashing. If not, that could be the problem causing water intrusion in that area. It may require destructive investigation to determine how to correct.
The other photos show a roof to wall intersection. It appears that the stucco joins the roof without proper counterflashing. Use your new tool (solid investigative probe), to determine if flashing exists behind the counterflashing, or if there is a counterflashing. There should be flashing at the wall as well as counterflashing (“Z” Bar) installed over the flashing.
We hope that this information will help you to identify the problem. We wish you the best success in identifying and solving the problem.
Your Friends at AskARoofer,
P.S. No one in this office will admit to naming the roofer tool.