Preheat the broiler. Line a sheet pan with foil.
Place the tomatoes on the prepared sheet pan and broil until charred, 4 minutes.
Add the oil to a large pot set over high heat. Saute the garlic, onions and oregano. Reduce the heat to medium.
Add the broiled tomatoes to the pot and mix into the sauteed onion mixture. Break up the tomatoes with the mixing spoon so they cook evenly. Add the broth, hot sauce and canned tomatoes to the pot. Season with salt and pepper. Sprinkle the cheese, reserving 2 tablespoons for garnish, into the soup. Use an immersion blender to blend the soup until smooth. Simmer the soup on low for 5 minutes.
Divide the soup among four bowls, then garnish with the reserved cheese and some Croutons.
Preheat the oven to 375 degrees F.
Place the cubes on a sheet pan in a single layer and sprinkle the oil over the bread. Season with salt and pepper. Bake until crisp and golden, about 10 minutes.