Hi Nick, Take it from a guy who has no talent.
Fiberglass repair is easy to do! I would go to U-tube and watch videos and and find an old boat that people were giving away on Craigslist to practice on. It's not hard at all to do. After laying a few sheets of fiberglass, I finished with a products called Easy Sand to smooth my work out. I was surprised how easy it was. You can do it ! I'd hate to see you lose your trailer over something like that. If you PM me , I can send you some pictures to show you how to do it. Good luck .
All the best, Monte