Combine the oil and the flour in a heavy stockpot or Dutch oven over medium heat. With a wooden spoon stir the mixture slowly and constantly. After about 5 minutes the mixture will begin to foam. Keep stirring. As the roux cooks, the color will darken and the flour will have a nice nutty aroma. It should take about 15 minutes to fully develop a nice dark brown roux.
When the roux is ready add the celery, onions and peppers (the Trinity) and cook for about 10 to 15 minutes. Once the vegetables have softened, add the bourbon and stir for 2 minutes, add chicken broth a little at a time to make sure the roux mixes well and is incorporated. Add the remaining ingredients, diced tomatoes, chicken, okra, bay leaves, Hot Sauce and season with salt and pepper.
Bring to a boil then lower heat and simmer uncovered for 1 1/2 hours, skimming off any fat that rises to the surface and stirring occasionally. In the last 7 minutes, add the shrimp and cook until no longer pink. At the very last minute add the fresh cilantro. Season with more salt and pepper, if necessary. Remove bay leaves and serve with rice and crusty flat bread.
Roughly chop the chiles and jalepenos discarding the seeds. Add to a food processor, along with the tomatoes, apple cider vinegar, garlic, sugar and salt. Process until desired consistency. If it's too dry add a little water. Pour mixture into a small saucepan and simmer for about 10 minutes. At this point you can strain it for a loose hot sauce or leave it as it is for a chunky hot sauce. Season with more salt, if necessary.
In a medium covered saucepan bring salted water to a boil. Add the rice, cover and lower the heat. Cook for 20 minutes until water is absorbed.