Trim, cut, pat dry and season the beef with salt and pepper. Coat the bottom of a large heavy Dutch oven with oil. Heat the oil, over medium heat, and brown the beef, in batches, being careful to not crowd. Add 1 tablespoon of oil, if needed, to finish the beef. As the beef browns, add it to a bowl and keep warm. Add 1 tablespoon of canola oil to the pot over medium heat and add the onions; cook for 3 to 4 minutes. Add the garlic, cook for 1 minute more, then stir in the stock to deglaze the pan. Add the browned beef, the vinegar and the water and cover tightly. Put the pot in the oven and after 45 minutes, give the beef a stir. Cover and cook for an additional 2 hours and 15 minutes, stirring every 30 to 45 minutes. Remove from oven and let cool for 20 to 30 minutes. Shred with forks, incorporating the onions and garlic.
When ready to assemble, put 1/2 cup enchilada sauce in the bottom of a 13 by 9-inch baking pan. Heat a medium saute pan over medium-high heat with just enough enchilada sauce to coat the bottom. Dip the tortillas, 1 at a time, into the sauce, and cook until tender, about 1 minute each. Combine the cheeses in a medium bowl. Remove the enchiladas to a flat surface. Fill each with some of the shredded meat and cheese, (reserve some cheese for the top of the baking pan). Roll and arrange them, seam side down, in the baking pan, packing the enchiladas tightly. Add additional sauce to come 1/3 up the sides of the enchiladas, then sprinkle a line of cheese, lengthwise, down the center of the pan. Garnish with green onions and black olives. Bake until bubbly, about 25 to 30 minutes. Remove from the oven, let sit for 5 minutes and then serve with sour cream.
Caesars Enchilada Sauce:
Add the boiling water to a large bowl and add all of the chiles. Let steep in water for 1 hour.
Transfer the chiles and the steeping liquid to a blender and puree for 3 to 4 minutes. Remove from the blender and strain through strainer.
Heat the oil in heavy saucepan over medium heat. Add the onions and garlic, saute until soft. Stir in the diced tomatoes, strained chiles, oregano, cumin, salt, black pepper and cloves. Cover, lower the heat and simmer for approximately 30 minutes.