Line a small baking sheet with foil; lightly grease the foil. In a plastic bag, combine the tomatoes, the 1 tablespoon vinegar, 1/4 teaspoon pepper, and 1/8 teaspoon salt. Seal and shake well to coat tomatoes with the vinegar mixture. Arrange tomatoes, cut side up, on the prepared baking sheet. Bake in a 425 degrees F oven for 20 to 25 minutes or until tomato skins are bubbly and dark red, but not burned. If you like, chop tomatoes.
In a screw-top jar, combine the oil, 1 tablespoon vinegar, herb, the 1/8 teaspoon salt, and the 1/8 teaspoon pepper. Cover and shake well.
Arrange the romaine on 2 chilled salad plates. Top with the mushrooms, cranberries, and pecans. Place tomatoes to side of salad. Pour vinaigrette over salad. Serve immediately.