This metal was struck by something, probably a tree limb. Causing the paint to be removed, letting the metal rust and create a crack/ hole.

We tightened the screws from 6 feet up the steep roof down and then all the way to the bottom of the lower slope roof. Well over 100 screws

Here are some areas I am concerned with in the future. I tried to push the wood back, but it just wanted to crack and start breaking, so we left it alone.

I’m not sure why but there were a lot of nails sticking out of the wood on the left side of the dormer.

We caulked under this metal as water could get in from the left side, and there was a hole on top of the rib. 

Another concern is this plumbing vent with no pipe boot at all. It relies only on a caulking adhesive to keep water out. Not a good idea

As you can see, this cabin is in the mountains, and there are a lot of trees in the mountains. There the gutters are packed with leaves.