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Cover potatoes with salted water in a large pot. Bring to a boil over medium-high heat. Simmer uncovered until tender, 15 to 20 minutes. Meanwhile heat 2 tablespoons butter and olive oil in a large sauté pan over low heat until melted. Add onions, cover, and cook, stirring periodically until soft and translucent, about 15 minutes. Remove cover, add sugar, season with salt and pepper and stir. Raise heat to medium-high and allow to caramelize, stirring often and adding water a tablespoon at a time if onions begin to burn, about 15 minutes longer. When potatoes are done cooking, drain in a colander and return to pan. Add remaining 5 tablespoons butter, milk, sour cream and cream cheese. Mash potatoes by hand using a potato masher, leaving some texture. Season to taste with salt and pepper. Fold in onions. Taste and adjust seasonings, if needed. Serve immediately, or store in the refrigerator for up to two days and reheat in a covered heavy dish in the oven or on the stovetop over low heat, stirring frequently.
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