Toast the guajillo, ancho, and árbol chiles in a dry skillet over medium heat for 30–45 seconds per side until fragrant and slightly darkened (watch them carefully so they do not burn). Transfer to a bowl, cover with hot water, and soak for 15 minutes until softened. Drain and set aside.
Add the rehydrated chiles, garlic, onion, pineapple juice, achiote paste, white vinegar, soy sauce, cumin, oregano, smoked paprika, black pepper, and salt to a blender. Blend on high until completely smooth. Taste and adjust salt as needed.
Place the wings in a large zip-lock bag or bowl and pour the marinade over them, tossing until every wing is fully coated. Cover and refrigerate for at least 2 hours, but overnight is even better.
Whisk together all the pineapple glaze ingredients in a small saucepan over medium heat and simmer for 3–4 minutes until slightly thickened and glossy. Set aside.
Preheat the grill to medium-high heat and make sure the grates are clean and well oiled. Remove the wings from the marinade and shake off any excess - too much marinade on the wings will cause flare-ups and burning on the grill.
Grill the wings over medium-high heat for 20–25 minutes total, closing the lid for the first 5 minutes then turning every 5–6 minutes until you get an even char on all sides.
In the last 5 minutes of cooking brush each wing generously with the pineapple glaze and flip once more so the glaze caramelizes directly on the grill grates.
In the last 2–3 minutes of cooking place the fresh pineapple slices directly on the grill alongside the wings and grill until caramelized and charred on both sides. Once grilled, discard the core and chop the pineapple into small pieces.
Transfer the wings to a platter and sprinkle the chopped pineapple slices over the wings. Finish with chopped fresh cilantro and thinly sliced green onion.
Serve immediately and enjoy!