Cut sausage into ¼” slices. Heat a large non-stick skillet over medium-high heat for 3 minutes. Add sausage and cook, stirring frequently, about 3-4 minutes or until lightly browned. Remove sausage and drippings from pan.
Reduce heat to medium. Place one tortilla in pan. Top with ¼ each of cheese, sausage, pineapple, green onions and black olives. Place another tortilla on top.
Cook quesadilla for 1-2 minutes or until bottom is crisp and lightly browned. Carefully flip quesadilla and cook second side 1-2 minutes until lightly browned and cheese is melted. Remove quesadilla from pan and repeat with remaining ingredients.
Cut each quesadilla into 8 wedges and serve with salsa, sour cream and chopped cilantro if desired.
