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Adjust an oven rack to the lower middle position and preheat the oven to 425°F. Use convection if you have it.
Combine the tomatoes, onions, garlic, sugar, ½ cup of the cream, tomato paste, oregano, pepper flakes, a big pinch of salt, and a few grinds of black pepper in a large saucepan or Dutch oven. Stir until the vegetables are coated in a tomato paste/cream mixture.
Transfer the pot to the oven and cook, uncovered, until the mixture starts to caramelize and brown around the edges, about 20 minutes.
Stir the mixture thoroughly and continue cooking until deeply caramelized and charred in spots, about 40 minutes total. (Don’t stir too frequently–the goal is to have some unevenness in cooking with a few very darkly charred spots and other lighter areas).
Remove the pan from the oven and add the remaining cream and stock.
Blend the mixture until smooth with a hand blender or a standing blender.
Adjust seasoning with salt, pepper, and vinegar, adding the vinegar a teaspoon at a time until the soup tastes bright.
Serve. Drizzle with olive oil and sprinkle with black pepper once it's in the bowl.