Preheat the oven to 425ºF. Line a baking sheet pan with parchment paper.
Heat a pan with 2 tablespoons of oil. Add pancetta, cook until golden brown and crispy, reserve the drippings (oil from the pan after cooking). Set aside. In a small bowl, mix pecans, a pinch of salt, and 2 tablespoons of maple syrup, stir to combine. Set aside
Place the squash and Brussels sprouts on a prepared pan. Add the remaining maple syrup, garlic powder, paprika, parsley flakes, salt, and, red chili pepper flakes. Drizzle with the remaining oil and the pancetta drippings. Toss to coat well.
Bake for 35 minutes or until fork-tender. Five minutes before they're completely done, take them out of the oven. Add crispy pancetta and pecan mixture, toss to coat well. Place them back in the oven and bake for 5 minutes. Serve warm.