"This is a mash-up of the classic diner sandwich and mexican grilled cheese—with the works." –Rach
In a large cast-iron skillet, heat the oil, one turn of the pan, over medium-high. Add the bacon. Cook, stirring often, until the fat begins to render, 2 to 3 minutes. Add the onion, chile, and garlic. Cook, stirring often, until the onion softens, 2 to 3 minutes. Add the turkey; season with salt and pepper. Cook, stirring occasionally and breaking up the meat with a spoon, until the turkey is browned, about 5 minutes. Season with the chili powder, coriander, cumin, and dried oregano. Add 1/2 cup water. Cook, stirring often, until the water is absorbed, 5 to 7 minutes. Reduce heat to low.
In a medium bowl, mix both cheeses with the crema.
Heat a large nonstick skillet or griddle over medium to medium-high. Spray 1 tortilla lightly with cooking spray and add to the skillet. Cook the tortilla until blistered in spots, about 1 minute. Flip the tortilla over. Top half of the tortilla with a quarter of the turkey filling, a few slices of avocado, some chopped tomato, and a quarter of the cheeses. Fold the tortilla over the fillings and cook, turning a few times, until the cheeses melt, about 2 minutes. Repeat with the remaining tortillas and fillings.
Cut the quesadillas into wedges. Top with pickled jalapeño slices and cilantro. Serve with lime wedges.