Using a wooden spoon or spatula, stir flour, salt, and yeast together in a bowl.
Add warm water and mix until most of the flour is moistened.
Using your hands, knead the dough in the bowl until a dough forms a sticky ball, about 1 minute.
Spray a 9-inch pie plate or cake pan with oil spray.
Transfer the dough to the prepared plate and press into a 7- to 8-inch disk.
Spray the top of the dough with oil spray.
Cover tightly with plastic wrap and refrigerate for 12 to 24 hours.
Place tomatoes in a fine-mesh strainer and crush with your hands.
Drain well, then transfer to a food processor.
Add oil, garlic, sugar, salt, oregano, and pepper flakes and process until smooth, about 30 seconds.
Two hours before baking, remove the dough from the refrigerator and let it sit at room temperature for 30 minutes.
Coat the bottom of a 12-inch cast-iron skillet with oil.
Transfer the dough to the prepared skillet and use your fingertips to flatten the dough until it is ⅛ inch from the edge of the skillet.
Cover tightly with plastic and let it rest until slightly puffy, about 1½ hours.
Thirty minutes before baking, adjust the oven rack to the lowest position and preheat the oven to 400 degrees Fahrenheit.
Spread ½ cup of sauce evenly over the top of the dough, leaving a ½-inch border.
Sprinkle Monterey Jack evenly over the border.
Press Monterey Jack into the side of the skillet, forming a ½- to ¾-inch-tall wall.
Evenly sprinkle mozzarella over the sauce.
Bake until the cheese at the edge of the skillet is well browned, 25 to 30 minutes.
Transfer the skillet to the stovetop and let it sit until the sizzling stops, about 3 minutes.
Run a butter knife around the rim of the skillet to loosen the pizza.
Using a thin metal spatula, gently lift the edge of the pizza and peek at the underside to assess browning.
Cook the pizza over medium heat until the bottom crust is well browned, 2 to 5 minutes (skillet handle will be hot).
Using 2 spatulas, transfer the pizza to a wire rack and let it cool for 10 minutes.
Slice and serve.
