Water logged ceiling,window nightmare

Homeowner noticed the water stains nearby his fireplace.
Stains could be seen on the ceiling tiles

This was taking place in more than one location

Water could be seen spilling over the rain gutter and onto the window.

Water damage rotting out the base of the window

The entire window sill was saturated with water and soft to the touch

Regular preventative maintenance could have prevented this issue

Solid and packed with debris,water will easily spill over.
In the middle of winter this would have been a nightmare.
Recipe for ice dam.All these were removed.
Downspouts disconnected.And re-attached.
No more water spilling over walkway

The entire 30 ft length was in the same condition

Above the fireplace.definitely a roofers view.
Water will follow a path

This could not be seen from the ground.

Failing caulk,basic maintenance goes beyond words.

snow and ice would have inflicted more damage.
loose wooden siding was re-fastened 

Urethane based caulk.CLEAR.
Ensures an appealing finished product.

This will prevent the boards from splitting any further.

When these openings are sealed will prevent moisture from  entering.
Water  normally flows inside the chimney housing and down the rafters.
The  close inspection goes a long way.
Basic maintenance will always pay in damage prevention.