Place oil in a large skillet or pot over medium-low heat. Add onion, carrot and garlic. Cook for 4-5 minutes or until vegetables are tender, stirring often.
Add sun-dried tomatoes, canned tomatoes, tomato soup, chicken broth, sugar, salt, pepper, oregano, basil and red pepper flakes. Bring soup to a boil for 2-3 minutes, then reduce heat and simmer for 30 minutes.
Remove soup from heat. Transfer soup to a blender. Add cream cheese and whole milk or half and half. Remove center piece from blender to allow steam to escape. Cover with a paper towel to prevent splatters. Process for a few minutes until smooth, making sure the soup is creamy (I would pulse it for at least 2-3 minutes in order to avoid it being chunky- trust me!).
Return mixture to stove and heat for 5 minutes. Add additional salt and pepper to taste. Place two large spoonfuls or orzo pasta in bottom of individual bowls. Ladle soup over and garnish with parmesan.