I have had the house on our fishing boat re-gelcoated (you don't want
paint on a commercial boat) and it turned out looking like new. My
paint and fiberglass guy sprayed it and then wet sanded it. He's a master at it, I wouldn't try it myself even if I had the gear. Matching the color is an art, and you have to find the right person to get it right. The same guy is spraying gelcoat on the decks of our Brewer 40 tomorrow, matching 20 year old white gelcoat (we removed the teak decks). If you find the right person, I think this is a viable way to go in your case where just the transom needs to be done.
Good luck, John