Begin by baking the chicken: Preheat the oven to 350 degrees. Place the chicken on a baking dish, and sprinkle it all over with a quarter teaspoon of the kosher salt, the black pepper, garlic powder, onion powder, and a quarter teaspoon of the paprika. Drizzle with one tablespoon of the oil, and bake for forty minutes, or until the chicken is no longer pink inside. Remove the skin and bones, and shred the chicken.
While the chicken is cooking, make the enchilada topping: Cook the bacon on low heat in a small skillet until it's nice and crispy. Drain and place in a small bowl. Stir in the cream cheese and the minced jalapenos, and ¾ a cup of the cheddar cheese.
Next, make the enchilada filling: In a large skillet, heat the rest of the olive oil on medium heat. Cook the onions and garlic until they're softened, for about five minutes. Then, add the tomatoes, chicken stock, heavy cream, cumin, chili powder, paprika, and a quarter teaspoon of kosher salt. Simmer about ten minutes, until the sauce is thickened. Stir in the shredded chicken.
In a bowl, mix together, the Monterey Jack cheese and 2¼ cups of the cheddar. Soften the tortillas in the microwave, on a plate, three tortillas at a time. Fill each tortilla with some of the filling and some of the cheese. Roll up the tortillas and place them seam side down in a casserole.
Spoon the topping mixture over the filled tortillas. Scatter the sliced jalapeno over the top and bake for 20 minutes at 350 degrees.