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Make the creamy jalapeño sauce. In a blender or food processor, combine the yogurt, mayo, lime juice, jalapeño, cilantro, green onions, and garlic powder. Season with salt. Blend on high until completely smooth, 1 to 2 minutes. Taste and add more salt as needed.
Make the quesadillas. In a large skillet set over medium heat, combine the beans, enchilada sauce, onion, chipotle peppers, and oregano. Season with salt and pepper. Cook, stirring occasionally, until the onion is soft and the sauce thickens around the beans, about 10 minutes. Remove the skillet from the heat.
To assemble, in a small bowl, toss together the pepper jack and Monterey jack. Set aside and reserve about 1 cup. With the tortillas arranged on a work surface, evenly layer onto one half of each the cheese, saucy beans, and cilantro. Sprinkle the reserved cheese on top, then fold the tortilla over to enclose the filling.
In a large skillet over medium heat, add a drizzle of olive oil. When the oil is shimmering, add the quesadillas, in batches, and cook, turning once, until the outside is crisp and golden and the cheese is melting, 2 to 3 minutes per side.
Serve the quesadillas hot, topped with the creamy jalapeño sauce, avocado, and more cilantro.