Preheat your oven to 400°F (200°C). Start by prepping the vegetables: dice up 12 fresh Roma tomatoes, one red bell pepper, two yellow onions, and two whole bulbs of garlic. Spread all of these ingredients evenly across a baking sheet. Next, add a few sprigs of fresh thyme for an aromatic kick. Drizzle 3-4 tablespoons of olive oil generously over the veggies, making sure they are well-coated to bring out their flavor during roasting. Season everything with salt, black pepper, and a pinch of cayenne pepper for a little bit of heat. Finally, spray about 1-2 tablespoons of balsamic vinegar on top, and sprinkle with 2 teaspoons of dried oregano. Place the baking sheet in the preheated oven and roast the mixture for about 1 hour until the vegetables are caramelized and tender.
Once the vegetables are done roasting, remove them from the oven and let them cool for a few minutes. Transfer the roasted vegetables, along with any juices from the baking sheet, into a blender. Add 4 cups of chicken stock and a handful of fresh basil leaves to the blender. Blend until the mixture is completely smooth. If you prefer a chunkier soup, you can pulse it a few times instead of blending it completely.
Pour the blended mixture into a large pot over medium heat. Add 2 tablespoons of butter, an additional cup of chicken stock (or more if you like a thinner consistency), and 1 teaspoon of sugar to balance the acidity of the tomatoes. Stir well and let the soup simmer for about 15 minutes to allow all the flavors to meld together. Finally, pour in 1/4 cup of heavy cream, stir, and allow it to warm through. Taste and adjust the seasoning with additional salt and pepper if necessary.
While the soup simmers, it's time to prepare the ooey-gooey grilled cheese sandwiches. Slice four pieces of sourdough bread, which will serve as the foundation of the sandwiches. In a small bowl, mix together a butter spread consisting of 1/4 cup of softened butter, 1/4 cup of grated Parmesan cheese, 1 teaspoon of dried oregano, 1 teaspoon of garlic powder, and a pinch of salt. Generously spread this butter mixture on one side of each slice of bread. For the inside of the sandwiches, mix together 1/4 cup of cream cheese, 2 tablespoons of mayonnaise, 1/4 cup of grated Parmesan, 1 teaspoon of oregano, and 1/2 teaspoon of garlic powder. Spread this mixture inside two slices of bread.
Place two slices of Colby Jack cheese and two slices of Cheddar cheese on top of the creamy mixture inside the sandwiches. Close the sandwiches and place them on a preheated skillet over medium-low heat. Cook each sandwich for about 3-4 minutes on each side until the bread is golden brown and crispy, and the cheese is fully melted and oozing out. The key to the perfect grilled cheese is cooking it slowly to allow the cheese to melt without burning the bread.
Ladle the warm tomato soup into bowls and serve alongside the crispy grilled cheese sandwiches. For an extra touch, garnish the soup with a sprinkle of fresh basil or a drizzle of cream. Enjoy your comforting fall meal while it's still hot and gooey!