Preheat the oven to 350 degrees F. Heat a large skillet over medium-high heat. Add 1 tablespoon of oil, the onion and pepper and cook, stirring, until soft, about 5 minutes. Add the ground beef, five-spice, 1 teaspoon salt and a few grinds of pepper. Cook, breaking up the meat, until it begins to brown, about 5 minutes. Stir in the tomatoes, olives and raisins. Bring to a simmer and cook until thickened, about 2 minutes. Season with salt and pepper.
Heat the remaining oil in a small skillet over medium heat. Once the oil is shimmering, heat the tortillas, one at a time, in the hot oil until they bubble and darken slightly, about 10 seconds per side. Drain on paper towels. Spread about 1/2 cup ground beef picadillo mixture on the bottom of a 9 -by-13-inch baking dish. Put about 1/4 cup picadillo and 1 tablespoon Cheddar down the center of each tortilla. Roll tightly and lay them in the baking dish, seam side down. Spoon the rest of the picadillo over the enchiladas and sprinkle with the remaining cheese. Bake the enchiladas until the tortillas are slightly crisp and the cheese is melted, about 10 minutes.
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