To dice the butternut squash, pierce with a fork. Cut off the ends. Microwave for 2-3 minutes (depending on the size.) Peel with a vegetable peeler. Slice in half. Scoop out the seeds. Dice.
Heat oil in a skillet over medium heat. Once hot, add the diced butternut squash. Add salt, pepper, and chili powder. Stir. Allow to cook for 15-20 minutes or until cooked through and browning.
Add kale. Cook until wilted. Remove from heat.
In another skillet (or remove butternut squash mixture, wash, and reuse), heat the skillet with a small amount of oil or butter. Lay down one tortilla. Top with 1 oz shredded cheese, 3/4 cup butternut squash mixture, 1/3 cup black beans, and another oz of cheese in that order.
Cook until golden brown. Flip. Cook again until golden brown. Repeat for the second quesadilla.