In a large pot of boiling water, add 1 tablespoon olive oil. Cook tortellini according to package directions until al dente. Drain and transfer to large bowl. Season cooked tortellini with salt and pepper. Add balsamic vinegar and 1/4 cup olive oil and mix to combine. Set aside. In a small bowl, add mozzarella balls, Italian seasoning, red pepper flakes, and remaining 1/4 cup olive oil. Mix to combine and set aside. Assemble skewers by layering one piece each mozzarella, salami, roasted red pepper, tortellini, basil, artichoke heart, and green olives.