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Heat a large skillet over medium high and add in the oil and ground beef. Cook, breaking up the beef as it cooks, for about 6-7 minutes until the beef starts to brown. Add the chipotle chili powder, garlic powder, paprika and salt and pepper and stir to combine. Cook for another 1-2 minutes until the spices are fragrant.
Stir in the chipotle salsa to the beef and continue to cook for another 2-3 minutes until everything is nice and saucy and the beef is browned and cooked through. Remove from the heat and set aside.
To make the dipping sauce: Stir together the sour cream, light mayonnaise, chipotle salsa and salt and pepper until fully combined. Taste for seasoning and set aside while you make the quesadillas.
Heat a clean skillet over medium low heat and place one tortilla in the pan, sprinkle the whole thing with ¼ cup of cheese and then about ¼ of the ground beef filling. Let cook for about 3 minutes until the cheese begins to melt, then fold the tortilla over to seal the quesadilla and press gently to flatten it. Let cook another 2-3 minutes, then flip and cook another 2-3 minutes, until golden brown and all the cheese has melted.
Repeat this process with the rest of the tortillas and fillings, cut the quesadillas into wedges and serve with the dipping sauce immediately.