Make the Potatoes; Adjust 2 oven racks to the upper and lower thirds position and preheat it to 450 degrees. On a rimmed baking sheet, toss the cut potatoes with 2-3 tablespoons of olive oil then generously season them with salt and pepper. Arrange potatoes cut side down on the baking sheet. Roast in the preheated oven, on the lower rack, until browned and tender, about 20-30 minutes.
Meanwhile, make the chicken; Pat chicken pieces dry with paper towels. Season the chicken generously with salt and pepper. Heat 2 tablespoons olive oil in a large cast-iron skillet over medium heat. When it begins to shimmer, add the chicken, skin side down and cook without moving until well browned about 3-5 minutes. Turn the chicken over and brown on the other side, adjusting the heat as needed, about 3 minutes. Remove chicken to a plate and set aside. Leave the oil in the skillet.
Add sausage to skillet and cook over medium heat, breaking it up into 1/2 inch pieces, until its browned, about 3 minutes. Remove sausage to a paper towel-lined plate and set aside. Remove skillet from heat and pour off all but 2 tablespoons of fat.
Return the skillet to medium heat and add the onions, red bell pepper, and garlic and cook, stirring occasionally, scraping up any brown bits on the bottom of the pan, until the vegetables are soft, 10-12 minutes. Add the wine and continue to cook, stirring occasionally, until most of the wine has evaporated about 8 minutes. Add broth, Peppadews, vinegar, and rosemary and bring to a boil. Reduce heat and vigorously simmer until slightly reduced about 5 minutes.
Add chicken back to the skillet, along with any accumulated juices, and nestle pieces into onion mixture. Place uncovered in preheated oven for 10 minutes. Add sausage to pan, pushing them down into onion mixture and continue to roast until chicken is cooked through, about 5-10 minutes and an instant-read thermometer inserted into the thickest part of the chicken reads 165 degrees.