Season the chicken breasts with pepper. Tightly wrap 2 strips of bacon around each chicken breast.
Heat a large ovenproof or cast-iron skillet over medium-high heat. Sear the chicken until the bacon is crisp, about 2 minutes per side. Drain any fat that accumulates in the pan.
Transfer the pan to the oven and roast until the chicken is cooked through and a thermometer registers 160 degrees, about 12 minutes. Transfer the chicken to a cutting board, tent it with foil, and let it rest for 5 minutes before slicing.
Divide the lettuce, tomatoes, avocado, and sliced chicken among 4 plates. Drizzle each with 1 Tablespoon of the barbeque sauce and 3 Tablespoons of the ranch dressing, and serve.
For the dressing, in a small bowl, whisk together the buttermilk, mayonnaise, chives, garlic powder, onion powder, dried parsley, and dried basil until combined. Season with pepper.