I like to eat these with make-shift guacamole which is basically ripe avocado mashed with salt and a little lime juice.
1 cup cubed and peeled winter squash, such as butternut, turban, or kabocha
3 tablespoons olive oil, divided
1/2 onion, diced
2 cloves garlic, chopped
1 red chile, optional
3 cups baby kale
2 cups queso fresco
4 flour tortillas
Heat oven to 425°F. Place squash on a baking sheet and drizzle with 1 tablespoon of the oil. Season well with salt and pepper and toss to coat in oil. Roast until golden and tender, about 15-20 minutes.
Heat remaining oil in a large frying pan over medium-high heat. Add onions, garlic, and chile, and season with salt and pepper. Cook until just tender, about 5 minutes. Add kale and cook until wilted, about 2-3 minutes. Taste and add more salt and pepper as needed.
Heat a dry comal or cast iron skillet over medium heat. Place 1 tortilla on the warm comal and top with half the squash, kale and cheese. Place the other tortilla on top. Once the bottom is toasted, carefully flip the quesadilla over and cook the other side until toasted and the cheese is melted. Repeat to make the second quesadilla. Serve immediately with make-shift guacamole.