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Prepare the following, adding each to the same large bowl as it is completed: Stem, seed, and thinly slice 4 large bell peppers. Thinly slice 1 small yellow onion. Thinly slice 3 garlic cloves.
Heat 3 tablespoons olive oil in a 12-inch high-sided skillet or a large Dutch oven over medium heat until shimmering. Add the bell peppers mixture, season with 1 teaspoon kosher salt and ¼ teaspoon black pepper, and cook, stirring occasionally, until the peppers are softened but still crisp-tender, 10 to 12 minutes.
Add 2 tablespoons tomato paste and sautè until the vegetables are coated and the paste darkens in color, 1 to 2 minutes. Pour in ½ cup water. Add 1 of the fresh oregano sprigs and ¼ teaspoon red pepper flakes, if desired. Stir to combine. Cover, reduce the heat to low, and simmer until the peppers are very soft and tender, 25 to 27 minutes.
Meanwhile, strip the leaves from the remaining 2 fresh oregano sprigs and coarsely chop.
When the peppers are ready, remove the pan from the heat. Discard the oregano sprig. Add 1 tablespoon balsamic vinegar and stir to combine. Taste and season with more kosher salt as needed. Garnish with chopped oregano. Serve warm, at room temperature, or cold.