HotShotHarry
Active VIP Member
If you look close at the second picture, you will notice that the drip edge does not reach into the eavestrough far enough. That is where the water is going behind the eavestrough and down the facia. The tough is too low at that point. It is not very difficult to remove the first couple rows of shingles and extend the shingle overhang. That roof vent should have been replaced but I would tar under the nearby shingles to ensure that they do not lift and also tar any exposed nails.