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1. Preheat oven to 450 degrees. Pour 2 Tbsp olive oil, red wine vinegar, garlic and herbs into a gallon size resealable bag, add chicken, season with salt and pepper then seal bag and massage mixture over chicken while working to evenly distribute herbs. Set aside and let rest while chopping veggies.
2. Place sweet potato, Brussels sprouts, apples and shallot on a large rimmed baking sheet. Drizzle with remaining 2 Tbsp olive oil then toss to evenly coat and season with salt and pepper to taste. Spread into an even layer then set chicken over veggie/fruit mixture. Sprinkle bacon (separate any pieces that stick together) evenly over veggie/fruit mixture.
3. Roast in preheated oven until chicken and veggies are golden brown, about 30 minutes (chicken should register 165 degrees in center). Broil during last few minutes for a more golden skin on chicken if desired. Sprinkle with more herbs and serve immediately.