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Preheat the oven to 400°F. Line a large rimmed baking sheet with aluminum foil, place a large wire rack in the center and lightly coat the rack with spray oil. In a medium bowl, toss fruit with maple syrup. Thread bacon and fruit onto 8 (10-inch) skewers, starting and ending with bacon, weaving a slice between 3 or 4 fruit chunks on each skewer as you go. (If using wooden skewers, soak in water for 30 minutes before assembling.) Reserve syrupy juices in the bottom of the bowl. Adjust ingredients to leave about 2 inches of empty space on either end of each skewer. Place kabobs on the rack over the baking sheet.
Bake for 15 minutes. (Bacon will crackle and pop as it renders fat, so be sure the rack is positioned well over the baking sheet to catch all drips.) Remove from the oven, carefully flip skewers and thread a mini waffle onto either end of each skewer. Drizzle reserved syrupy juices over kabobs, return to the oven and continue to cook until bacon is just crisp and waffles are golden, about 10 minutes more.