Heat 3 tablespoons oil in a skillet over medium heat until it ripples. Add onions, peppers and garlic; season with salt and pepper, and cook to very soft and tender, 20-25 minutes. Remove from heat and cool.
Arrange the meat on parchment or plastic in a single layer with a bit of space between slices. Top with another sheet of plastic or parchment, and gently pound to 1/16-inch thick; season with pepper.
Working on a cutting board, shingle or layer 3 to 4 slices of meat to form a 7- to 8-inch square. Cover with cheese and even layer of cooked onions, peppers and cherry peppers. Roll up and secure with cut kitchen string. Repeat to form 5 more rolls.
In a shallow dish, whisk together Worcestershire, soy and 2 tablespoons oil. Roll meat in sauce and marinate 15 minutes.
In a small pot, warm consommé or stock and season with oregano.
Heat a large, cast-iron skillet over medium-high heat. Add remaining tablespoon oil, 1 turn of the pan. Shake any excess marinade off the rolls and add to the skillet. Brown and crust the meat rolls and cook 5-6 minutes for a medium-rare center and crispy outer layer; remove to cutting board.
While the rolls cook, cover potatoes and garlic with cold water in a medium pot. Bring potatoes to a boil, salt water and cook potatoes to fork-tender, about 8-10 minutes. Drain and return to hot pot.
Add marinade to pan and a half cup of warm consommé or stock, spoon mixture back into consommé stock pot to include the pan drippings in the dipping sauce.
Add stock (or dipping sauce), vinegar, rosemary, pepper and EVOO to the potatoes. Adjust seasoning to taste.
Cut string off beef rolls and cut each roll into 4 pieces. Arrange pinwheels upright on plates, 6 cut pieces per person. Serve each portion with some potato salad and a small bowl of dipping sauce.
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