Rustic Roasted Heirloom Tomato Soup with Balsamic Vinegar and Blue Cheese

Name: Rustic Roasted Heirloom Tomato Soup with Balsamic Vinegar and Blue Cheese
Ingredients: 5 pounds mixture of heirloom tomatoes, big juicy ones are best!; 2 tablespoons garlic, divided; 1 1/2 teaspoons kosher salt, divided; 1 1/2 teaspoons pepper; 1 1/2 teaspoons sugar; 5 tablespoons olive oil, divided; 3 cups chopped yellow onion; 1 red pepper, chopped; 3 poblano peppers; 1/3 cup finely chopped basil, plus more for garnish; 1/4 cup balsamic vinegar, divided; 1 tablespoon sherry; 1 ounce crumbled gorgonzola blue cheese, divided