Using a fork, mash avocados in a medium bowl until chunky. Add onion, lime juice, tomato, 1 tablespoon cilantro, and salt; mash to desired consistency. Set aside.
Preheat waffle iron to high. Coat interior with cooking spray. Place 1 tortilla on waffle iron. Mound 1/3 cup cheese in the center, and spread cheese evenly, leaving a 1/2-inch border. Add 1 1/2 ounces chicken and 1/2 teaspoon cilantro. Place a second tortilla over filling, and close waffle iron. Cook until quesadilla is golden brown and heated through, 2 to 3 minutes, keeping an eye on it so the cheese doesn’t ooze out.
Remove quesadilla from waffle iron; repeat 3 times with remaining tortillas, cheese, chicken, and cilantro. Cut into wedges; garnish with cilantro. Serve quesadillas hot with guacamole and, if desired, salsa and sour cream.
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