1 cups (or more) olive oil, divided
2 pounds plum tomatoes, halved lengthwise, seeded
1 1/2 teaspoons dried oregano
3/4 teaspoon sugar
1/2 teaspoon salt
1 to 2 garlic cloves, minced
2 teaspoons minced fresh Italian parsley
Aged goat cheese (such as Bûcheron)
1 baguette, thinly sliced crosswise, toasted
Preheat oven to 250°F. Pour 1/2 cup oil into 13x9x2-inch glass or ceramic baking dish. Arrange tomatoes in dish, cut side up. Drizzle with remaining 1/2 cup oil. Sprinkle with oregano, sugar, and salt. Bake 1 hour. Using tongs, turn tomatoes over. Bake 1 hour longer. Turn tomatoes over again. Bake until deep red and very tender, transferring tomatoes to plate when soft (time will vary, depending on ripeness of tomatoes), about 15 to 45 minutes longer.
Layer tomatoes in medium bowl, sprinkling garlic and parsley over each layer; reserve oil in baking dish. Drizzle tomatoes with reserved oil, adding more if necessary to cover. Let stand at room temperature 2 hours. DO AHEAD Cover; chill up to 5 days. Bring to room temperature before serving.
Serve with aged goat cheese and toasted baguette slices.