Combine 2 tablespoons port, apple, and next 4 ingredients (apple through sugar), stirring well.
Cut a horizontal slit through thickest portion of each pork chop to form a pocket. Stuff about 1/4 cup apple mixture into each pocket. Sprinkle pork evenly with 1/2 teaspoon salt and pepper.
Heat a large nonstick skillet coated with cooking spray over medium-high heat; add 4 pork chops. Cook 7 minutes on each side or until done. Remove pork from pan; keep warm. Repeat procedure with remaining pork.
Combine 1/2 teaspoon salt and flour in a medium bowl, stirring with a whisk. Gradually add 3 tablespoons port and broth, stirring with a whisk. Add mixture to pan, scraping pan to loosen browned bits. Bring to a simmer over low heat; cook 5 minutes or until thick, stirring constantly. Serve sauce with pork.