Puerto Rican Pasteles (Pasteles Puertorriqueños)

Ingredients:
6 large tomatoes (about 3 pounds), coarsely chopped
1 medium green bell pepper (about 6 ounces), cored, seeded, deveined, and coarsely chopped
1 medium yellow onion (about 8 ounces), coarsely chopped
8 garlic cloves, peeled
20 Caribbean sweet peppers (ajíes dulces), seeded and cut in half
1/2 cup tomato sauce
1/4 cup coarsely chopped cilantro
2 broad-leaf culantro leaves
1 1/2 tablespoons cider vinegar
1 teaspoon dried oregano
1/4 cup achiote-infused extra-virgin olive oil
8 ounces slab bacon, rind removed, cut into 1/4-inch dice
1 1/2 pounds boneless pork shoulder or butt, cut into 1/2-inch dice
1/4 cup chicken broth
1/3 cup whole milk
1 1/2 pounds malanga, peeled and cut into 1-inch cubes
1 1/2 pounds green bananas, peeled and thickly sliced
"1/2 green plantain, peeled (see Cooks notes) and thickly sliced", 8 ounces calabaza (West Indian pumpkin) or Hubbard or kabocha squash, peeled, seeded, and cut into 1-inch cubes
1/4 cup achiote-infused extra-virgin olive oil
1/2 to 1 teaspoon salt, or to taste
"Twenty-five 12-inch plantain leaf squares (4 to 5 packages; see Cooks notes for how to prepare)", 1/4 cup achiote-infused extra-virgin olive oil
Twenty-five 42-inch pieces of kitchen twine
1/3 cup dark raisins
One 15-ounce can chickpeas, drained and rinsed, or 2 cups cooked chickpeas
"2 medium red bell peppers (about 6 ounces)
roasted (see Cooks notes)
peeled
cored
seeded
and cut into 1/4-inch-wide strips"
50 pimiento-stuffed olives
cut in half

Instructions:
Place all the ingredients in a blender or food processor and puree. Set aside. DO AHEAD: You can make the seasoning base (recado) the day before.
Heat the oil in a 12-inch skillet over medium heat. Add the bacon and brown for 2 to 3 minutes. Add the pork and cook, stirring, until it begins to release its fat, about 15 minutes.
Stir in the recado, reduce the heat to low, and cook, covered, for about 50 minutes, or until the pork is tender when pierced with the tip of a sharp knife. Add some chicken broth if the sauce thickens too much during cooking. When the meat is done, transfer it to a plate with a slotted spoon. Set the sauce aside. DO AHEAD: You can make the sofrito the day before.
Working in 2 or 3 batches, puree the milk, malanga, green bananas, green plantain, and calabaza in a blender or food processor and pour into a large bowl. Add the oil and salt and mix well to color the masa evenly. Stir in the reserved sauce. Taste for seasoning and set aside.
Place one plantain leaf square on a work surface with the veins perpendicular to you. Brush generously with achiote oil. Place 3 heaping tablespoons of masa in the center of the leaf and spread into a 6-inch square, leaving a 3-inch margin on all sides. Place 3 tablespoons of the diced pork on top, forming a rectangle. Garnish with 4 raisins, 4 chickpeas, a strip of red pepper, and 4 olive halves. Tie the tamal following the instructions for the pastel wrap (see Cooks' notes). Repeat with the remaining wrappers and ingredients. DO AHEAD: You can prepare the plantain leaves the day before.
Using two steamers (or working in batches), steam for about 1 hour (see Cooks' notes).