Combine sugar and cinnamon in small bowl. Reserve 1 tablespoon sugar-cinnamon mixture; set aside.
Spray large skillet with cooking spray. Add apples; cook over medium heat until tender, stirring occasionally. Remove from heat; stir in remaining sugar-cinnamon mixture, raisins and rum extract. Top each tortilla evenly with cheese to within 1/2 inch of edge. Spread apple mixture over cheese. Spray medium nonstick skillet with cooking spray; heat over medium heat until hot. Place 1 tortilla in skillet, filling side up, and heat 1 minute. Remove from skillet; quickly fold in half. Cover and keep warm while heating remaining quesadillas.
To serve, cut quesadillas into 3 wedges. Sprinkle with reserved 1 tablespoon sugar-cinnamon mixture. Sprinkle quesadillas lightly with confectioner's sugar, if desired.
Top tortillas as directed. Place 1 to 2 tortillas, filling sides up, on waxed paper. Microwave on HIGH (100% power) 30 to 60 seconds until warm. Remove from microwave; quickly fold in half. Cover and keep warm while microwaving remaining quesadillas. Serve warm.