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Preheat the oven to 425°F. In a small bowl, stir together the garlic, oregano leaves, fennel, 1 tablespoon salt, and ½ teaspoon pepper. Place the pork, fat side up, on a rimmed baking sheet. Rub all over with the garlic mixture.
Roast until fragrant and sizzling, 20 minutes. Reduce heat to 300°F and continue to roast for 1 hour.
Remove the sheet from the oven and arrange the peppers and onions around the pork. Drizzle with oil and season with ½ teaspoon each salt and pepper. Tuck oregano sprigs around the vegetables and return to the oven. Roast until the vegetables and pork are very tender, 2 to 2½ hours more.
Transfer pork to a board and let rest for 10 minutes before slicing. Arrange pork and vegetables on a platter, and drizzle with vinegar and any pan juices from the baking sheet.