Preheat the oven to 500°F for at least 30 minutes while you make the dough and/or prepare the fillings. Line a heavy-duty rimmed baking sheet with parchment paper.
In a medium bowl, whisk together the vinegar, garlic, oregano, and olive oil until the mixture is well combined. Add the olives and roasted red pepper, stir well, and season to taste with salt and pepper. Set the olive salad aside while you roll out the dough.
Dust a clean work surface with flour. If you're making one large calzone, roll out the pizza dough into a 12-inch round. If you're making four individual calzones, divide the dough into four equal-size portions, shape each one into a ball, and roll them out into 6-inch rounds.
To fill the calzone(s): If you're making one large calzone, layer the meats, then the olive salad, and finally the provolone on the bottom half of the dough round, leaving a 1-inch border of dough. If you're making four individual calzones, layer the filling ingredients (first the meats, then the olive salad, and finally the provolone) in the center of the dough rounds, leaving at least a ½-inch border of dough all the way around.
Brush the naked edges of dough lightly with water and fold the calzone(s) in half to cover the filling. Press the edges together, then crimp them with your fingers to create a tight seal.
Transfer the filled calzones to the prepared baking sheet. Brush the top(s) with olive oil, cut small steam vents in the top(s) using a small, sharp knife, and place them in the oven. Bake for 15 to 20 minutes or until the calzone(s) are golden brown.
Remove the calzone(s) from the oven and let them rest for 5 to 10 minutes before slicing. (The large calzone should be cut into eight pieces; the individual calzones can simple be cut in half or served as is.) Serve the calzones with marinara sauce for dipping.