So who guessed it right? 
May no longer be leaking. You have said that it is dry now (guessing you checked with moisture meter) so the cold temp you are seeing is not related to Water at present. My guess it is not insulated or the insulation was matted down (possibly when it got wet). Thermal Imaging does not See Water or Moisture, It sees Temperatures. The image looks more like areas lacking insulation to me.
Kind of like a metal detector “sees” metal. You need other clues to figure out if it is gold or an aluminum pull tab. The first time a person uses a (top of the line, professional, discriminating) metal detector will dig up every pull tab till they gain experience and learn how the Instrument works and it’s limitations…and then you pass by the pull tabs.
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The gutters have leaf guards. They had some minor debris accumulated, but probably much better off than having open gutters with so many pine trees. Homeowner did not mention any leaks associated with snow… only rain. Where the house is is about 3,000 to 4,000 elevation. When it snows, while it can get one foot or more at once, it quickly melts and never stays for very long.
I do not know the answer. I was fishing for ideas to help my client. I recommended that the homeowner hire a roofing specialist to do some destructive investigation (start lifting shingles). The prevailing opinion on this topic seems to be that the roof defect is likely to be nearby the leak location. I passed that onto the client in a follow-up email, also mentioning that I used this forum to get some professional input (help). I expressed my hope that the leak can be found and repaired, along with the other smaller issues with the roof. The roof is 18 years old - still has some life on it. If they can say with confidence that they found the leak and got it repaired it will do a lot to reassure would-be buyers. They gave me a five-star review. I will try to circle back to this topic if I find out anything about where the leak was found.
I did use a moisture meter. Moisture content was about 3% - normal. David Andersen helped me (us) interpreting the thermal image. The blue area above the leak is very likely to be the sunlight shadow from the chimney stack. I believe it even has a mushroom shape. The dark walls could be lack of insulation, but the fact that it was 10:30 AM and the walls were still cold being shaded from the sun all morning, could also be the major contributing factor. The ultra dark spots at the leak location are likely the change in emissivity due to the wood decay, combined with the fact that I was using the FLIR C5 MSX setting on the camera that blends the infrared with a HD standard camera image for more picture detail. So, in this case, the thermal image did not provide us with any new information, other than the sun is powerful and some porch ceilings have little or no insulation.
My guess is that it’s the rain causing the leak. 
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How do you mark a thread “Solved”… 
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Nope. Send me your money? 
Well. if you know how to use it, it will tell you a lot…
I’ll second that!
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