Preheat the oven to 350 degrees F.
For the Seasoned Flour: If you are making the seasoned flour, simply mix together the flour, salt, and the peppers together in a bowl. Dust the chicken with the flour, shaking off any excess. Reserve.
For the Chicken: In a large skillet, cook the bacon in the canola oil over medium heat, until it has rendered some of its fat. Add the chicken in batches, skin side down and sear, 2 minutes per side, turning once, until golden on all sides. Transfer the chicken to a roasting pan fitted with a rack; set the skillet aside. Bake the chicken for 25 to 35 minutes.
For the Curry Sauce: Set the skillet you seared the chicken in over medium-high heat and add the garlic, Scotch bonnet, and red onion. Stir well to coat and cook until caramelized, about 10 minutes. Add the curry powder, stir well, and cook for 30 seconds. Add the orange juice, star anise, and saffron and cook, stirring for 2 minutes, as the juice reduces by 1/2.
Add the chicken stock and stir, then add the vanilla bean, bay leaf, and coconut milk and stir. Bring to a simmer and cook for about 20 minutes until the sauce thickens enough to coat the back of a spoon.
While the sauce is simmering, put the cucumber in a colander and toss with salt. Let stand for 20 minutes, stirring now and then to distribute the salt. (The salt will pull excess water out of the cucumber.) Rinse the cucumber well under cold running water and drain. Blot with paper towels.
Pass the curry sauce through a fine-mesh strainer into a smaller skillet. Add the tomatoes and heat through. Keep warm over very low heat.
To serve, put 2 pieces of chicken on each plate. Spoon the curry sauce over and scatter the cucumber and pineapple over the top.
You can substitute 1/2 cup all-purpose flour seasoned with kosher salt and freshly ground black pepper.