Tenant Says a Leak is Causing Moisture in Walls

[Scott J.]

I've had a long-term tenant that keeps my single family rental in immaculate shape. Sometimes she sends requests that are aesthetic only and aren't really necessary, but that's because she is so keen on keeping the place looking great. Otherwise her requests are all reasonable. 

She recently texted me a handful of requests, one of which has me concerned. She said it looks like there's a leak in the wall near the roof and sent the photo below. 

We called our licensed contractor who said the leak is coming from the roof, which he doesn't do, and the moisture doesn't appear to be in the wall. He said we should have him power wash the stucco and call a roofer to fix the leak. 

We call a roofer, who gave us a quote of $900 and said he'll come out and patch the roof in two weeks. After one day with minimal rain, the tenant texted me again and said she sees new signs of water damage inside the loft (interior of what you see above). These are her photos. 

I can't really make out what's in the photos, but am taking this seriously due to moisture. What are the right steps from here to protect myself and get this taken care of appropriately for the tenant? Who to call to fix? What to tell the tenant? Should I pay the contractor to power wash the stucco? 

[Thomas S.]

Once the roof is repaired have the tenant keep an eye on the interior wall through a few rain storms. If the wall dries up have a contractor repair the drywall if necessary and repaint the wall