Heat a large cast iron skillet and add the canola oil. When the oil begins to smoke lightly, add the tomatoes in a single layer. Season with salt, to taste, and add the sugar. You want to blister the skin slightly, drawing out water from the tomatoes, to intensify their flavor. Continue cooking on low heat.
In a soup pot, heat 1 tablespoon of the olive oil and add the garlic, shallots, and red pepper flakes. Season with salt and pepper. Add the oregano and stir to blend. Allow to cook, over low heat, until the shallots and garlic become tender and translucent, 3 to 5 minutes. Add the canned tomatoes and the water. Turn the heat down to medium and cook until the tomato flesh starts to lose shape, 12 to 15 minutes. At this point, the soup should be mushy and blender-ready. If there are still some hard pieces, add a little more water and cook for a few additional minutes. Taste for seasoning.