Preheat oven to 400F and brush a baking sheet or ceramic baking dish with oil.Cut pumpkin into 8 wedges and scrape out pulp and seeds. Brush wedges with 2 tablespoons olive oil and season with salt and pepper. Bake until soft, about 45 minutes, then remove the skin and cut into 1/2 inch cubes. Set aside.In a large pot over medium heat, heat remaining oil until shimmering. Add onion and cook until translucent, about 5 minutes. Add jalapeno, garlic, chili powder, cumin, oregano, cinnamon and chipotle powder and cook until fragrant, about 1 minute.Add ground beef and cook until no longer pink, 7 to 9 minutes, breaking up clumps with the back of a wooden spoon.Stir in the pumpkin, canned tomatoes, water, cocoa powder, salt and pepper, and bring to a boil. Reduce heat and simmer for 45 to 60 minutes, until slightly thickened.Add chopped chocolate and stir until melted. Serve immediately.Serves 6. Each serving has a total of 15.6 g of carbs and 5.6 g of fiber. Total NET CARBS = 10 g.
