Water is not a friend of most building materials. In general, it's a good idea to get water away from your home as quickly and efficiently as possible.

Note in this photo that the gutter is directing water directly against the siding. Rather than repair the gutter, a piece of flashing was nailed to the chimney. Water has run down the siding and is now growing moss. Masonite siding has a particularly difficult time staying stable under high moisture conditions.

Also note the inappropriately sized shutters on the addition. Even if they are inoperable (for decoration only), shutters should be sized so that they would cover the window when closed. In most cases, appropriately sized shutters should be the same height as the window and half the width.