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To me the mast step does not look like a problem. I would be willing to bet that it on the better side of 50% of all Whalers (if, you back that up with Jay's suggestion of insuring that the bolts still bite, etc, etc, )
From the limited pictures you have posted, more of a concern to me would be the motor mounting if you plan on using it. According to the drawings of the underlying wood structure there is NO support for a motor mount on that side of the transom. ( http://www.ruach.net/HarpSpec.html ) The wood plate that is under the glass for the original is just not there on the starboard side.
The (apparent) damage to the bottom edge of the transom does not appear to be significant unless the underside is much worse and the laminate is showing considerably more. From the pix, the boat actually looks quite nice compared to a lot of others we collectively have commented on. I would be (always) more concerned about the bailer area, and the integrity of the sides of the thru-holes. That is a major source of problems with regard to water getting into the hull and de-laminating the foam/glass bond and rotting the underlying wood.
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