Preheat the oven to 400°F.
In a small saucepan, heat the water, sugar, vinegar, and salt. Place the onions in a heatproof bowl, cover with the vinegar mixture and cool to room temperature.
Heat 1 tablespoon olive oil for the beef in a large skillet. When hot , add the beef and cook, breaking it up into smaller pieces until no longer pink. Remove the meat to a plate. In the same skillet, add another tablespoon of olive oil and the onion, bell pepper, garlic, oregano and cumin. Cook for 5 minutes, or until tender. Add the bay leaf, crushed tomatoes, wine, tomato paste, raisins, olives, capers, salt and pepper and bring to a simmer. Simmer for 10 minutes. Add the beef back to the skillet and simmer for 15 minutes, until most of the liquid is reduced. Remove the bay leaf.
Meanwhile, place the rice, 2 cups of water and a pinch of salt in a saucepan. Bring to a boil, reduce the heat to a simmer, cover and cook for 20-30 minutes, until the grains are tender. Remove from the heat and stir in the black beans.
On a baking sheet, toss the roma tomatoes, jalapeños, and yellow onion with the canola oil. Roast for 10-15 minutes, until browned. Transfer to a blender, along with the remaining roasted salsa ingredients. Blend until smooth and season to taste.
Heat 1 inch of canola oil in a skillet to 375°F. Add the plantains, working in batches, and fry until golden, flipping once. Transfer to a paper towel-lined plate to drain.
To serve, divide the rice between bowls. Top with beef and plantains and serve with salsa and pickled red onions on the side.