Pepperoni Pizza Salad

Name: Pepperoni Pizza Salad
Ingredients: 12 ounces tomatoes, any variety or color, sliced into 1-inch wedges or smaller; Kosher salt; 1 large head (about 16 ounces) iceberg lettuce; 3 ounces pepperoni (pork or turkey is fine); 6 ounces low-moisture mozzarella, torn or chopped into bite-sized pieces; 3 ounces (about 2 heaping cups) store-bought or homemade croutons; 4 tablespoons red wine vinegar, divided; 4 tablespoons extra-virgin olive oil, divided; 2 teaspoons honey, divided; 2 teaspoons dried oregano, plus more for serving (optional); 1/2 teaspoon red pepper flakes, plus more for serving (optional); Freshly ground black pepper; Grated parmesan, for serving (optional)