In braising pan over medium high heat, warm 1/4 cup olive oil. Add chicken and cook, stirring, until browned on all sides, about 5 minutes. Add onions and cook to brown, about 5 minutes more. Reduce heat to medium; stir in garlic. Add tomatoes, chicken stock and chipotle chili. Cook chicken, stirring, about 15 – 20 minutes, or until almost all of the liquid is absorbed. Add coffee and chocolate; cook to absorb about 5 – 8 minutes more.
Remove chicken mixture from pan; place in on baking sheet to cool. Add cilantro, cumin, salt and pepper; toss well to combine
Between two tortillas, place about 4 tablespoons chicken mixture and 3 tablespoons shredded cheese. Warm 2 teaspoons olive oil in same pan that cooked chicken mixture. Add quesadilla to pan and cook to brown on each side, about 2 – 3 minutes per side.
To serve, cut quesadilla into quarters. Top with guacamole and cilantro sprig.
In small bowl, combine 1 ripe avocado, peeled and pitted; 2 tablespoons white onion; juice from one-half lime; ¼ cup water; and 1 teaspoon Kosher salt. Mash with fork and blend well.