Place the bacon in a saute pan and bring to a medium-low heat. Add the olive oil and cook the bacon until brown and crispy, about 10 minutes. Remove the bacon to paper towels. Save the fat.
Working with one sheet at a time, lay out the puff pastry on a clean dish towel. Brush the puff pastry with the reserved bacon fat, and then with some maple syrup, leaving a 1/2-inch border along the side furthest away from you. Combine the granulated sugar and cinnamon in a small bowl and sprinkle the brushed area liberally with cinnamon sugar. Top with half the crispy bacon and raisins.
Beat together the egg with 1 teaspoon water in a small bowl. Brush the border with egg wash. Starting with the side closest to you, roll the puff pastry into a long log, using the towel to help you. Press firmly to close the log, arranging the seam on the bottom. Cut the log crosswise into 6 equal pieces. Repeat with the second sheet.
Brush a 6 1/2-by-9-inch baking dish with the remaining bacon fat. Snuggle the 12 rolls into the baking dish. Brush the tops of the rolls with the remaining egg wash. Bake until the rolls are puffy and golden brown, about 25 minutes.
For the glaze: Combine the powdered sugar, milk and a little bit of the remaining maple syrup in a small bowl until it reaches a frosting-like consistency, adding more milk if necessary. When the rolls come out of the oven, slather them with the glaze.