Preheat the oven to 450°F (232°C). Position one oven rack in the upper-middle section and another in the lower-middle section.
Place the onion wedges on a sheet pan. Toss with 2 tablespoons olive oil and ½ teaspoon kosher salt. Arrange the garlic halves cut-side down on the same pan.
Place the pan with the onion and garlic on the upper-middle oven rack.
On a second sheet pan, toss the Roma tomatoes with the remaining 2 tablespoons olive oil and ½ teaspoon kosher salt. Place this pan on the lower-middle rack.
Roast for 15 minutes. Rotate the sheet pans between the racks and continue roasting for approximately 15 minutes, or until the tomatoes and onions are soft and beginning to brown around the edges.
Remove both pans from the oven and allow the vegetables to cool slightly.
When the garlic is cool enough to handle, gently squeeze the roasted cloves from their skins into a blender.
Add the roasted tomatoes, onion, and any flavorful juices from the sheet pans to the blender. Pour in the broth and add the oregano, smoked paprika, and red pepper flakes.
Blend until completely smooth and creamy.
Pour the blended Roasted Tomato Soup into a pot and bring it to a gentle simmer over medium-low heat.
Stir in the half-and-half, if using. Taste and season with additional salt and black pepper as needed.
Serve hot with grilled cheese, toasted bread, or crunchy croutons.