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Mix warm milk, mashed potatoes, shortening, white sugar, eggs, and salt together using an electric mixer in a large mixing bowl. Sprinkle yeast over mixture and stir gently until yeast is dissolved and well mixed. Add flour 2 cups at a time to milk mixture using an electric mixer until dough becomes thick. Set aside mixer and add flour gradually, kneading dough on a work surface by hand until it is smooth and no longer wet and sticky. Place dough back into the mixing bowl and cover with a wet cloth. Set in a warm place until dough has doubled in size, about 1 hour. Roll 1/2 of the dough out onto a floured surface into a rectangle shape, about 1/2-inch thick. Repeat with remaining dough. Mix brown sugar and enough milk to make a paste together in a small bowl. Smooth paste evenly across both dough rectangles and sprinkle generously with cinnamon. Sprinkle with raisins. Roll dough rectangles up and slice into 1 1/2-inch sections. Place rolls into 7 greased pie pans, gently pressing down using your fingers to squish into pans. Set rolls in a warm place until puffy, 30 minutes to 1 hour. Preheat the oven to 350 degrees F (175 degrees C). Bake rolls in the preheated oven until light brown, 10 to 15 minutes. Meanwhile, bring brown sugar and butter to a boil over low heat in a saucepan, stirring constantly, for 2 minutes. Stir in milk and return to a boil. Remove from heat and let cool to lukewarm temperature, about 5 minutes. Gradually add powdered sugar until thickened. Beat using an electric mixer until it reaches a spreading consistency, adding warm water or additional milk if frosting gets stiff. Remove rolls from the oven and let cool, 10 to 15 minutes. Frost and serve.