I'm thinking of breeding him to a Captain Treacherous broodmare, what do you think/
What's the maternal breeding? There's so much to this-----the mare's size, confirmation, speed, traits, what were her strengths and weaknesses, and so on. Then, what kind of stallion will compliment that-----both pedigree and individual. If I were you, I'd take a bunch of pictures, get a bunch of videos of her racing, and call Bob Marks, and ask him what he would charge for a breeding consult.