Prepare the olive salad: In a medium bowl combine vinegar, olive oil, garlic and Italian seasoning. Whisk until well combined. Set aside. Chop remaining olive salad ingredients and add to bowl. Toss well until combined and coated. Refrigerate for 30 minutes (up to overnight).
Meanwhile: Prepare the cheeseburger: Sprinkle beef patty with salt and pepper on both sides. Grill patties about 3 minutes on the first side until browned and slightly charred. Cook for about 5 minutes on the second side for medium. Take off grill and allow to rest for 5 minutes.
Cover bottom half of bun with ΒΌ cup of olive salad. Place burger on top. Layer cheeses and meats and place bun on top.