Fresh hail damage and insufficient ventilation on architectural shingle roof

In the first photo, you can see that there are no dents or protrusions from the bottom side of the gutter. From the top side, you can see dents in the soft metal gutter guards. These took the brunt of the impact and masked the presence of hail damage from underneath.  You will notice in the second photo that there are very little shingle granules in the gutters. This is a sign that this hail damage is fresh. As hail damage ages, granules slide off the roof and fill up the gutters leaving the asphalt and fiberglass beneath the granules exposed to the elements.

In the top photo, you can see the discolored areas on shingles known as spatter. When you look closer, you can see that not only the granules are missing in some places but also the asphalt, leaving the fiberglass totally exposed.  The fiberglass mat is not water-resistant, allowing water to pass through the shingles causing leaks.

Here, you can see that substantial sized hail has dented the vent hood.  Imagine what this can do to your shingles!

Here, the shingles appear to have some damage around the chimney. The decking is spongy and likely rotten in this area. Some of the bricks are beginning to crumble.