[Finster]

Thats a tough one. I had a boat with that problem and I couldn't cure it with cabosil, fairing or chopped glass, from the outside. What needs to be done is, it needs to be worked from the inside out. Or you'll have lay so much glass on the outside that it would make it impossible to fair out.

Start with adjusting your trailer so that doesn't happen anymore and see what a professional has to say.

That particular area is like an Achiles heal for boats.

Good luck.