Tinner, that is weird that the shingles leak and you cant even see the darn hole! Frustrating indeed. My shingles dont even lift up really and I have no idea how they overlapped but it doesnt look as think as yours does. I still don't know how it is gonna do in just rain storms because i haven't monitored it in the attic in the summer,,,,cause the roofer said it was just a freak occurrence.
I do see the same gap where the shingles start that you show in the pick, it runs diagonal in some spots and looks iffy to me.
Handy man, Thanks for the advice, I am not sure if I have drip edge on my roof into gutter or if it is right or not, but I have a side pic of gutter above is second set of pics. That leak on the brick was happening 1-2 days after the snow thawed completely and roof and gutters were wet. Its like the ice dam was melting under the felt paper and running along sheathing but no clue how it got on brick. I cannot see the soffit from attic due to those foam air baffles.