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For the tofu feta, drain excess water from tofu and press it between paper towels to dry.
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Cut tofu into ½-inch cubes. Whisk vinegar, lemon juice, milk, basil, garlic, and salt in a glass container with a fitted lid. Submerge tofu cubes in mixture, place lid on container, and refrigerate.
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Marinate tofu for 3 hours or overnight for a stronger flavor.
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For the creamy cucumber dressing, shred cucumber. Place in a sieve or double layer of cheesecloth and squeeze out excess water. Place cucumber and remaining ingredients in a high-powered blender and blend until very smooth. Set aside.
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For the salad, preheat oven to 400 degrees. In a baking dish, toss potatoes with olive oil, oregano, salt, and pepper. Bake for 45 minutes, tossing once halfway through, until roasted and golden brown. Toss warm potatoes with cucumber, bell pepper, tomatoes, onion, olives, pepperoncini, and tofu feta. Drizzle with creamy cucumber dressing, sprinkle with black pepper and oregano, and serve immediately.