Preheat oven to 425 degrees.
Mix Italian seasoning and garlic powder and rub over pork chops. Place chops into a foil lined baking dish and bake for 10 minutes. Flip over and bake an additional 10 minutes; making sure that the insides are no longer pink. Remove from oven and cover with foil to keep warm.
While pork chops bake, cook bacon until crispy. Crumble into a small bowl; set aside.
Wash and cut potatoes into 1/2-inch pieces. Peel garlic cloves.
Place the potatoes and garlic in a large saucepan or Dutch oven and fill with water to just cover potatoes. Boil over high heat for 10 to 12 minutes or until potatoes are tender when pierced with a fork. Drain water; mash with a fork or potato masher.
Stir in the cream cheese, butter, milk, salt, and pepper until well combined. Stir in cooked and crumbled bacon pieces.
Toss together the salad greens, cherry tomatoes and diced apples. Drizzle with your favorite dressing.
Serve pork chops with mashed potatoes and salad.