Place the steak in a glass dish. Sprinkle the steak on both sides with salt and pepper. Let stand at least 15 minutes and up to 1 hour to tenderize, turning the steak occasionally.
Heat the oil in a large, heavy skillet over high heat. Add the steak and saute to desired doneness, about 3 minutes per side for rare. Transfer the steak to a cutting board. Let rest 5 minutes. Slice thinly across the grain.
Place 4 tortillas in the skillet with the pan juices and heat over medium-high heat, working in batches if necessary. Place 1/2 cup cheese on top of each one and top with 4 ounces sliced meat. Place the remaining 4 tortillas on the top. Cook until the cheese start to melt, about 2 minutes. Flip and cook until golden and the cheese is melted, another 2 minutes on the other side.
Remove the quesadillas from the skillet. Peel open the quesadilla and spoon about 1/2 cup Roasted Tomatillo and Apple Salsa on top. Close the quesadilla and slice into quarters. Serve with Eva's Chunky Guacamole.
Preheat the oven to 350 degrees F.
Place the tomatillos, apples, garlic, onion and jalapenos on a baking sheet. Toss with the olive oil, 2 teaspoons salt and 1 teaspoon pepper and roast until the tomatillos are softened and slightly charred, about 20 minutes. Peel the garlic. Puree all the ingredients in a blender until smooth. Season with salt and pepper. Makes 3 1/2 cups.
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In a large bowl, place the avocados, tomatoes, onion, cilantro, serrano, lemon juice, and salt, to taste. Stir gently until well combined. Transfer to a serving bowl and serve.
Cook' s Note: To keep the guacamole from turning brown, press a pit from one of the avocados into the center of the dish. Remove it before serving.