Cracks in the stanchion pockets can be easily repaired from the inside of the boat by sanding the area around the crack and epoxying a small piece of fiberglass cloth over the crack.

When you store the boat for the winter (outside) you should cork the stanchion holes (after making sure there's no water in them), or even fill them with anti-freeze and cork them. Otherwise water can freeze in the holes and crack the stanchion pockets. It's a common but not a serious problem in cold weather areas of the country.