Take a wooden skewer and push it directly in the middle of the pineapple.
Slice the pork shoulder into about 1-centimeter (¼ in) slices, then transfer to a large dish or bowl.Combine the pineapple, serranos, 2 diced small red onions, 1/2 cup chopped cilantro, 2 tablespoons lime juice, 2 teaspoons kosher salt and 1/2 teaspoon pepper in a bowl toss. Soak 2 to 3 thinly sliced serrano chiles in ice water, 10 minutes, then drain. Finely chop the pineapple, removing the core. Peel 2 pineapples and cut into 1/4-inch-thick planks grill until marked, about 3 minutes per side. Dip a tortilla in the chile mixture, then add to the skillet and cook until lightly browned, 1 minute per side. Heat 2 tablespoons vegetable oil in a nonstick skillet over medium heat.
Transfer the chiles to a blender and add 4 cups water, 5 garlic cloves, 1 diced onion, 2 teaspoons each chicken stock and kosher salt, 1 teaspoon each pepper and dried oregano and 1/2 teaspoon cumin puree. Soak 20 dried guajillo chiles in warm water at least 30 minutes drain.Top with cotija, chicharrónes, cilantro and radishes. Assemble the tacos: Arrange the pork on the tortillas and top with the pineapple-serrano salsa and tomatillo salsa.Cut the pork into 1/4-inch pieces and return to the braising liquid, tossing to coat. Remove the pork from the braising liquid and transfer to a cutting board let rest at least 10 minutes. Transfer the pork to the oven and roast, covered, 3 hours. Make the tacos: Place the pork in a large roasting pan and pour the marinade on top cover with foil and refrigerate at least 4 hours.Transfer to a blender and add the pineapple juice, orange juice, apple juice, beer, vinegar, oregano, paprika, annatto, cloves, 2 tablespoons salt and 1 tablespoon pepper puree until smooth. Add the chiles, onion and garlic and cook, stirring, until the onion is translucent, about 5 minutes. Heat the vegetable oil in a medium saucepan over medium heat. Make the marinade: Soak the dried chiles in warm water until softened, about 15 minutes drain.Serve with pineapple, chopped onion, and cilantro. Chop pork coarsely into small pieces against the grain.Cook marinated pork in the hot pan, turning once, until browned, 4 to 5 minutes. Wipe out grill pan and preheat over medium-high heat.Cook remaining pineapple slices on a ridged grill pan over medium-high heat until slightly blackened and soft, about 5 minutes per side.Marinate pork in the refrigerator, 4 hours to overnight.Pour blended mixture over pork, ensuring all sides are evenly coated. Arrange pork slices in a glass or ceramic baking dish.Combine tomato flesh, softened chile peppers, 2 slices pineapple, orange juice, quartered onion, vinegar, chipotle peppers, salt, garlic, cloves, cumin seeds, and oregano in a blender blend until smooth.Add guajillo and ancho chile peppers cook until softened, about 5 minutes.
Remove from heat and cool until easily handled. Cook tomato on a ridged grill pan over medium-high heat until slightly blackened, about 5 minutes.
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