Combine red wine vinegar and brown sugar in a saucepan; cover and bring to a boil. Reduce heat and simmer until sugar is dissolved and mixture is slightly thickened, 5 to 10 minutes.
Heat a large skillet over medium heat; cook and stir bacon until crisp, adding 3 dashes liquid smoke while cooking, 5 to 10 minutes. Transfer bacon to a paper towel-lined plate and drain bacon grease.
Place potatoes, skin-side down, in a baking dish. Drizzle 1 tablespoon olive oil over potatoes and season with salt and pepper.
Bake in the preheated oven until tender, about 20 minutes.
Mix apples and bacon into vinegar-brown sugar mixture; bring to a boil. Add garlic, reduce heat to low, cover, and simmer for 30 minutes.
Heat remaining 2 tablespoons olive oil in a skillet over medium-high heat. Season chicken with salt and pepper and place in the hot oil; cook for 7 minutes. Flip chicken;add water and a few shakes liquid smoke. Cover skillet and cook until chicken is no longer pink in the center, about 10 minutes more. An instant-read thermometer inserted into the center should read 165 degrees F (74 degrees C).
Place chicken on a serving plate and top with apple mixture. Arrange potatoes alongside chicken.