---

For any hole drilled, the top should be beveled slightly so it's like a Y. This reduces the force of the screw from cracking the gel coat.

I am a little concerned in seeing the long cracks on the transom. I doubt these were caused by overtightened engine bolts. It could be the transom took a hit (fell off a trailer, landing in the skeg or some type of shock.

Given that they are only in the gel coat, I say route them out a bit (dremel type tool) and fill with gel coat.