Combine vinegar and maple syrup in small saucepan; bring to a boil.
Reduce heat slightly and stir occasionally until reduced by half.
Set aside.
Dice squash into 1-inch cubes.
Slice onion into small wedges.
Combine squash and onion on a rimmed baking sheet
Drizzle with 1 tablespoon oil and toss to coat fully.
Bake for 15 minutes.
While squash and onions cook, dice pancetta into small pieces
Heat frying pan over medium; cook diced pancetta for 3-5 minutes or until crispy.
Drain pancetta on paper towel lined plate.
Dice apple into 1-inch cubes.
Coat with ½ tablespoon oil; toss.
After baking for 15 minutes, remove tray from oven.
Add apple to tray, and bake for an additional 5 minutes.
Transfer squash, onion, and apples to a large bowl.
Pour reduced dressing over it; stir well.*
Top with pancetta.
Serve.
Notes
At this point you also can transfer the salad to a preheated, nonstick frying pan. Heating the salad in the pan will allow the sauce to caramelize on the veggies.