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Peel and seed the avocados and place in a medium bowl. Use a fork or a masher to roughly mash the flesh. Add the lime juice and a pinch of salt and stir to combine. Stir in the sour cream and chipotle peppers. Taste for seasoning and adjust if needed. Refrigerate until needed.
Heat a large skillet over medium heat. Add the chorizo and cook until completely separated, about 5 minutes.
Season the shrimp with salt and pepper, then add to the pan with the chorizo, pushing the chorizo to the side. Cook until pink, about 2 minutes, then flip over and cook another minute until the second side is pink. Remove from the heat.
Place another large skillet over medium heat. Add a drizzle of olive oil. Place one of the tortillas in the pan and cook for 30 seconds, then turn over. Add ¼ of the cheese to ½ of the tortilla, then layer on ¼ of the shrimp and chorizo. Fold the tortilla over. Cook until the bottom is browned and the cheese is melting, then flip over and cook until the second side is browned. Remove to a cutting board and repeat to make 3 more quesadillas.
Cut each quesadilla into wedges and serve with the smoky guacamole.