Cook the bacon in a medium skillet set over medium heat until crispy, about 8 minutes. Transfer the bacon to a paper-towel-lined plate to drain. Add the garlic and 2/3 cup of the oil to the skillet with the bacon drippings. Reduce the heat to medium-low and cook, stirring occasionally, until the garlic is golden, about 7 minutes. Remove from the heat and set aside to cool.
Meanwhile, peel the potatoes and slice the potato skins into very thin strips (the thinner you cut the strips, the crispier they will be). Toss the strips with the remaining 1 tablespoon oil, 1/4 teaspoon salt and a few grinds of pepper in a small bowl. Spread in an even layer on a rimmed baking sheet and bake, stirring once, until golden and crispy, about 15 minutes.
Cut the peeled potatoes into 1-inch chunks and put in a saucepan. Cover with cold water by about 2 inches and add a generous pinch of salt. Bring to a boil over high heat; reduce the heat and simmer until the potatoes are tender, 15 to 20 minutes. Drain and allow to cool slightly. Pass the potatoes through a ricer into a medium bowl or mash with a potato masher until smooth.
Pour the oil and garlic mixture into the bowl of a food processor and process until smooth. Add the potatoes, vinegar, 1/3 cup water, 1/2 teaspoon salt and a few grinds of pepper and pulse until just creamy and combined; do not overprocess or the potatoes will become gluey. Add up to 3 tablespoons more water if necessary so that the dip is soft and spreadable. Season with additional salt and pepper.
Transfer the dip to a serving bowl and top with the sour cream. Crumble the bacon and sprinkle it over the dip. Top with the Cheddar, crispy potato skins and scallions. Serve warm or at room temperature with potato chips, red bell pepper strips and celery sticks.
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