Farmstand Tomato Soup with Arugula Pesto

Name: Farmstand Tomato Soup with Arugula Pesto
Ingredients: 10 medium or 4 very large ripe tomatoes (about 4 pounds), cored; 1/4 cup olive oil; 2 shallots, coarsely chopped; 2 cloves garlic, chopped; 1 (28-ounce) can fire-roasted crushed tomatoes; 1 tablespoon kosher salt; 1/8 teaspoon sugar; 1/4 to 1/2 cup heavy whipping cream; 1/4 cup good-quality vodka (optional); 1/2 cup pine nuts; 5 ounces baby arugula; 2 cloves garlic, coarsely chopped; 1/2 teaspoon kosher salt; 1 tablespoon freshly squeezed lemon juice (about 1/2 medium lemon); 3/4 cup extra-virgin olive oil; 1/2 cup freshly grated Parmesan cheese