@toxcrusadr:Thanks for the info about the wires. I've been working on this for the last few days. With the help of the scope that came today, an additional flashlight, and a camera I think I located the leak. I got a very clear photo and it looks like it is a very narrow line of water on the wood that slopes down from the very top of the roofline. Hopefully that is the only leak point! I left a message with the roofer that I was planning to hire this week, just asking for a patch or tarp even if they couldn’t re-roof for 5 or 6 weeks, but did not get a call back. Spoke to another roofer who will be over on Monday and assured me that all the steps I’ve taken so far are corrrect (thanks to everyone who replied here and google), and advised me on a couple more things I can do to prevent damage, including your pie pan idea. What kind of caulk did you use? That might get me through the weekend. @morz8: Thanks to you as well! Wow, a tree falling must have been scary. I’m glad your beautiful ceilings were spared! I wish I was able to get such a quick response. Not for lack of trying, I’ve been on the phone for days! I don’t mind living with a tarp as long as my interior is protected from further damage. I will update as things progress.

I am a little skeptical a new roof would cause the damage you describe. But let's assume this was the case. You have to convince the roofer his work caused the water damage and ask him to pay for all the repairs. He if agrees, all is good. If he doesn't then you could file a claim with your homeowner's insurance company. If the damage is covered you may still have to pay the deductible. You ask the roofer to pay the deductible, and if he refuses take him to small claims court if you want full recovery for your loss.

It doesn't look like there is an adequate solution for you. There's probably some issues and responsibilities about who owns what and which wall, it looks like 3 coming together here. The gap looks to be about 2" wide, too small to get anything in there or down in between. You can see the collection of all the debris washing down from their tiled shingles, if not already there will be so much organic material collected in that gap down at the ground it will retain moisture and that will translate through your wall. And stink. Besides, no matter what you do, their pitched roof will still route water and debris up against your vertical wall. Their roof needs a cricket built to route the water the other (perpendicular) way. As a temporary stop gap, you "could" put a flashing tucked under their 2nd shingle and up your wall. However, the water is still coming straight to the wall, so it will backup under their shingles and cause lots more trouble for both of you.

Hey Matt - that's a lot of cake frosting, and usually you don't want to do that, or you will be making yearly treks up on the roof to putty more on. I see you used DAP Roofing Sealant, which is asphalt based. You do not use that in contact with a rubber boot. It should be a poly or silicone. They also make a "boot rain collar" that slides over the top of the pipe and covers the integral flashing boot. Other than the original deteriorated boot and frosting, the continuing leak could be anything. The silicone dab on the 3 nails, the shingle cut too close to the metal boot, or something up higher than this vent penetration.