Roasted Tomato Soup

I love tomato soup and noodles with grilled cheese. When I was growing up, it was the official Halloween night dinner in our house. I still occasionally enjoy a bowl of tomato soup from the can, but when I found this recipe from Voila! I decided it might be time to try a grown up version of the soup I love so much. We served this along with grilled cheese, using pepper jack. Our overall opinion of this dinner was that it was alright, but I am not rushing to make it again. It was quite expensive, since tomatoes are not in season right now. $10 of tomatoes from the grocery store, and I ended up dumping the leftovers after not eating them for a few days. :(

3 1/4 pounds Plum Tomatoes, sliced in thirds
3 tablespoons Olive Oil, plus more for sauteeing
1 (28 ounce) can Diced Tomatoes
6-8 Garlic Cloves, left unpeeled
1 1/2 teaspoon Salt, divided
1 teaspoon Pepper, divided
1 Onion, finely chopped
1/2 teaspoon Oregano
2 teaspoons Brown Sugar
4 cups Vegetable Broth
3/4 cups Heavy Cream (*Joel would have liked if I left this out)
1/4 teaspoon Cayenne Pepper
Pinch of Red Pepper Flakes
Pinch of All Spice

Arrange the tomatoes, cut side up, in 1 layer on a large cookie sheet and add garlic cloves. Drizzle with olive oil and sprinkle with salt and pepper. Roast tomatoes and garlic for 1 hour at 350 degrees, then cool in the pan. When the tomatoes and garlic have cooled, peel the garlic. In a large soup pot, cook onion, oregano, and sugar in butter over moderately low heat, stirring frequently, until the onion is softened, about 5 minutes. Add the tomatoes, garlic, and broth. Simmer, covered, for 20 minutes. Puree soup using an immersion blender. Stir in cream, salt, pepper, all spice, cayenne, and red pepper flakes to taste. Simmer for 2 minutes and serve.