In a large bowl gently toss together the tomatoes, oregano, 1 Tbsp oil, garlic, 1 1/2 tsp salt and sugar. All to sit (and macerate) for 1 hour at room temperature.

Drain mixture through a sieve, over a large measuring cup to collect the liquid. Press firmly with a spatula to remove as much juice as possible. Reserve juice, then divide tomatoes into 2 bowls. Pulse one of the mixtures a few times using a food processor or immersion blender until mushy. Set aside.

Use a heavy bottom pot like a 4-6 quart Dutch oven to boil the pasta (this type of pot prevents burning/food sticking to bottom). Add in the 3 cups of water, the pasta, and the reserved tomato juice (need 1 cup-add water to top it up if necessary), and a bit more salt if desired (1/2 tsp). Cover and cook over medium-high heat, stirring often until pasta is al dente, and most of the liquid has evaporated, about 15 minutes.

Remove from heat and stir in remaining ingredients, along with the 2 tomato mixtures, and remaining 2 Tbsp of oil. The heat from the pasta will warm the tomato mixture perfectly.