Agave-Glazed Pork Belly with Grilled Pineapple
['1 4-pound pork belly (with or without rib bones)', '4 teaspoons kosher salt plus more', '2 teaspoons freshly ground black pepper plus more', '6 poblano chiles, stemmed, coarsely chopped', '3 habanero chiles, stemmed, sliced into 1/4" rounds', '3 serrano chiles, stemmed, chopped', '1 cup agave syrup (nectar), divided', 'Vegetable oil', '1 ripe pineapple (about 3 1/2 pounds), peeled, cored, cut into 1/2" rounds', '1/4 cup apple cider vinegar', '"Ingredient info: All chiles are available at better supermarkets', 'farmers markets', 'and Latin markets. Agave syrup (nectar) is available at better supermarkets and natural foods stores."']
Preheat oven to 250°F. Season pork belly all over with 4 teaspoons salt and 2 teaspoons pepper.
Place chiles in a large roasting pan. Place pork belly, skin side down, on top of chiles; drizzle with 1/2 cup agave. Pour remaining 1/2 cup agave and 2 cups water into pan. Cover pan tightly with lid or two layers of foil.
Transfer to oven and cook pork for 3 hours, basting with pan juices every hour. Turn pork over. Cook until very tender, about 4 more hours.
Transfer pork to another roasting pan (if bone-in, remove and discard bones). Strain liquid from first roasting pan into a saucepan (there should be about 5 1/2 cups); reserve chiles. Gently boil juices until reduced to about 1 1/4 cups, 45-50 minutes; add reserved chiles. Remove pan from heat. Let glaze cool; chill.
Meanwhile, cover pork with parchment or waxed paper. Top with a large plate. Place weights, such as large canned goods, on top. Chill overnight.
Reheat glaze. Build a medium-hot fire in a charcoal grill, or heat a gas grill to high. Brush grill rack with oil. Grill pineapple until nicely charred, 2-3 minutes per side; place on plates.
Let grill cool to medium heat. Slice pork belly into 1"-thick pieces. Grill until warmed and crisp, about 3 minutes per side. Brush pork with some of the glaze from chile sauce.
To serve, place 2 or 3 pineapple slices on each plate; spoon glaze over, then top with pork belly. Drizzle with vinegar.
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