Cook chicken by desired method. I recommend poaching for the best texture.
While the chicken cooks, go ahead and add olive oil to a skillet over medium-high heat. Add olives oil and onion. Sauté until softened. Add garlic towards the end and continue to sauté until fragrant.
In a stand alone mixer, add the cooked chicken, seasonings, onions, garlic, and chipotle peppers to the mixing bowl. Mix on low until chicken is fully shredded. Once shredded, add the crushed tomatoes and continue to mix on low until fully combined.
Set a large skillet over medium heat. Add a little olive oil then a tortilla. Top with a handful of cheese, 1/4th of the chicken mixture, then fold over to seal. Heat until cheese is starting to melt and bottom side is browning. Flip and continue to cook until cheese has fully melted and the center is hot. Repeat this with remaining ingredients until you have four quesadillas.
Cut the tortillas into four portions each. Stack on a serving platter and serve with guacamole, sour cream, salsa, cilantro, and jalapeños. Serve immediately.