The damage was caused by the strakes going up and over top of the rollers. They weren't contacting any other part of the trailer. This isn't an issue if you guide the boat onto the trailer and winch it up.
Thanks Scott. Didn't see that stickied post before. In reading that, seems like I should be good with using CSM in 2-3 layers for this type of repair since the area is more likely to take impacts?
I got a new to me Stealthcraft jet sled recently. The previous owner used to power load it onto the trailer, and apparently never realized the strakes were wearing down on the rollers in doing that. They kept slapping gel coat over the damage instead of a full repair. There's also a small patch...