Ok... just went up there with hubby and tried to look for this, but we're not sure what we should be seeing. The shingles are under the brown metal strip (is that the J-channel??), so we can't lift the edges to look under. Hubby said he can see another strip of metal if he looks between the shingles and that brown metal strip.
Here are 2 pics I took up there. The brown caulking is what we added earlier today, along the portion of the roof where there was all sorts of old cracked dried up caulk that was already there. It seems like the bottom 4 feet or so were heavily caulked before, the rest of the way up looks clean and clear. We did NOT run the hose all the way to the top, but we probably should to confirm that this area is the only problem. There are NO leaks on the other side of our dormer either, which looks identical. No signs of it being caulked over there before either.
This first picture is right where the caulked area begins. The brown is what my husband added, but you can see the thick clear caulk underneath. I believe that was from the previous owner, not our roofer, because it appeared very old (roof was just 6 mos ago) and also was not adhered to shingles.
And this is along where the problem is. Again, my husband added the brown and you can see all the lumpy clear caulk on the inside part of the brown metal strip too, right against the siding. He added some on top of what was there, but tried to smooth it out the best he could. Whoever did it before left it looking really awful and lumpy... It was piled in there pretty good. :/ That's probably not good.
So I guess my question now is - what exactly SHOULD this seam look like? If our roofer didn't do something properly, what is it we should ask him to do? And will we be expected to pay for more work, or should this have been included in our roof replacement? (He did remove the old shingles, there is just one layer there).
Also - the space between that brown strip and the siding... where is the water going that gets inbetween there??
thanks again for your help everyone, I really appreciate it.