sorry to see the problem with the transom. I was worried when I first saw your pic of the outside skin cut off. Not the best way to do it. People think its faster and easier than cutting the cap and going from the inside but then its all on you to shape it.
Question. Could it be that the holes are drilled in the wrong place or angled incorrectly? If you remove the bottom bolts and snug the top, can it sit flush?
Second.
Rather than shave it, consider adding to it to make a flat surface. Way easier. Use some EPOXY hard filler.
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