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Set out a large 14-inch sauté pan, or a 6 quart pot. Set over medium heat. Add the oil to the skillet. Once hot, add in the ground beef, garlic, onions, and Italian seasoning. Salt and pepper liberally. Break the meat apart with a wooden spoon. Stir and sauté until the beef is cooked through and the onions have softened.
While the beef is cooking, peel and chop the potatoes.
Add the canned tomatoes to the skillet, plus 1 additional can full of water. Then stir in the chopped potatoes and crushed red pepper. Stir and simmer for 15+ minutes until the potatoes are fork-tender. (Add extra water if needed.) Taste, and season with additional salt and pepper if needed. The consistency of the dish should be thick yet slightly saucy. Serve warm with a good sprinkling of cheese over the top.