This was a roof only inspection for a realtor who has used me several times. She is in litigation over the roof and asked me to weigh in on it. She has seen several examples of leakage I believe in the first year after it was installed. I was only able to pick up moisture around the chimney that was definitely high-in the 80 to 90 percent range. It’s definitely sloppy in places but other than that and the moisture around the chimney, i don’t have too many “smoking guns” as I like to call them. This is an old half double with solid board sheathing. The uneven nature of that can be seen in the shingles occasionally. It probably should have had plywood over top of it but honestly I don’t see that often around here unless its skip sheathing originally. If you have a moment, I would appreciate any opinions. Obviously at the outset a six year old roof of this quality shouldn’t be leaking but any other critiques are welcome.
Thank you.
A common entry point would be around the windows over the porch roof and then running down the sidewall behind the headwall flashing over the pouch, and most roofers don’t know how to flash a chimney correctly. Just saying. 
Did the realtor point you in any direction? And yes the chimney flashing in your pic looks improperly done.
IMO, all visible areas of flashings are crap!!
I also see that the metal snow guards have exposed nails that are not sealed.
I think I’m going to start calling you by the nick name " Hawk Eye" Bridges… 
Ok. Thanks for all of that guy’s. I appreciate it.
I would be very careful when getting involved with possible litigation. Looks to me like the seal strips are exposed. Shingle are not overlapped as they should be. Just what I can see in the photos.
Cheers
I guess maybe.
That is the shadow line built into the shingle, high definition shingles.
I was leary about the litigation aspect. What lessons have you learned Douglas?
What is a half double?
Looks like the chimney flashing directs runoff beneath the shingles.
Kinda odd how they wove the bottom three courses at the valley base.
Scott, how can you SEE the nails in the avalanche preventers!
I zoomed in on pic 2. O, no I looked again and I may be wrong, they could be rivets and not nails.
When I zoom in it just pixilates.
I don’t think those snow guards have nail holes there. If I remember right they only attach at the top.
When I zoom in with my PC it very clear, but I looked again and they are rivets and not nails.
The guard is riveted onto a slotted bar, which is underneath the shingles.
https://www.google.com/amp/s/www.bestmaterials.com/amp/detail.aspx%3FID=20881
A half double is a large house split exactly down the middle so that there are two separate residences. The shared wall in the middle is generally where the steps are and you can hear your neighbor clomping up and down the steps. In older houses like this one you can actually go up into the attic and walk across to your neighbor’s attic and potentially visit them through their hatch 
. The reason I mentioned it is because both sides of the double were done at the same time. I asked her neighbor if they had been complaining and she said that they don’t pay attention to their home so I assume that means that they haven’t had a problem. I also thought it odd that the bottom of the valleys had been woven.
In the attic I could see where they used aluminum as sheathing where it was probably rotted near the eaves. It’s a bunch of smaller things that I guess can lead to a premature failure of the roof or things that can’t be realistically fixed until the roof is ripped off and re done. That’s basically how I see it. Agree or disagree?
I really don’t know what you want us to tell you from the pics that you cannot see yourself 
Did you actually go up on this roof? if you didn’t, there is no way you would inspect it properly from the pics alone. There are very critical details I would check that cannot be seen from these pics. If you cannot think of what they are, I would be deferring this to someone else. Someone needs to get up on that roof and do a proper inspection. A binoculars/drone/camera pole is a very “limited” inspection. When a roof is “leaking” it’s time to get more involved and a mere remote visual inspection is no longer going to be any good unless the roof looks completely out of whack.
Dan, if you can get set up for it, if you want to do it ay all, a hose with warm water on the roof with someone coordinating where to spray and some one inside with a good quality (320 x 240 pixels, or so) shooting images, where the outside guy is spraying, with the infrared imager would go a long way to finding the leak.
But there may be more damage done, so the homeowner needs to know you are not responsible for that.
It is kinda like Bubba (Mark Andersen) does to find some basement/crawlspace leaks.
Personally, I would turn it over to a roofing contractor that uses an Infrared Imager, unless you like being inside a courthouse a lot. LOL!
I hope you can work it out whatever you choose to do and retain your connection.