1. Preheat oven to 400 degrees. Line a large baking sheet with parchment-paper lined aluminum foil; set aside.
2. Rub potatoes with oil and season with 1/2 teaspoon salt and 1/8 teaspoon pepper. Place on prepared baking sheet and bake until fork-tender, 1 hour to 1 hour and 10 minutes. Remove from oven and let stand until cool enough to handle. Potatoes can be cooked up to 1 day in advance, wrapped and refrigerated until ready to use.
3. Place bacon in a medium skillet over medium heat; cook, stirring occasionally, until bacon is crisp and fat is rendered, 5 to 6 minutes. Transfer to a paper towel-lined plate to drain.
4. Peel one potato; discard skin and place pulp in a large bowl. Cut the top quarter from each of the remaining 4 potatoes and using a spoon, scoop pulp from potatoes into bowl, leaving a 1/4-inch layer of pulp around the skin. Return potato shells to baking sheet.
5. Using a handheld masher, mash pulp until smooth. Add 1 cup cheese, sour cream, butter, bacon, chives, and remaining 1 1/4 teaspoons salt and 1/2 teaspoon plus 1/8 teaspoon pepper; mash until smooth. Spoon potato mixture back into potato shells, top with remaining cheese and bake until potatoes are hot and cheese is melted, about 15 minutes. Serve immediately.
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