Heat 1 Tablespoon oil in a large skillet over medium heat then add sliced onions. Cook over medium heat stirring every so often until golden brown and caramelized, 20-30 minutes. Can be made up to 3 days ahead of time.
Meanwhile preheat oven to 400 degrees then line a baking sheet with parchment paper, or foil sprayed with nonstick spray. Add butternut squash, remaining Tablespoon oil, salt, and pepper then toss to coat and spread into an even layer. Roast for 15-20 minutes, or until squash is caramelized but not mushy, flipping with a spatula halfway through. Can be made up to 3 days ahead of time.
Combine black beans, water, chili powder, cumin, dried oregano, and cayenne pepper in a small saucepan over medium heat then heat through. Can be made up to 3 days ahead of time.
Heat a griddle or skillet over medium heat then place down 1 tortilla. Sprinkle on 1/4 cup cheese then layer on a quarter of the roasted butternut squash, seasoned black beans, and caramelized onions. Top with another 1/4 cup cheese then place another tortilla on top and cooke until golden brown on both sides. Slice with a pizza cutter then serve with Lazy Girl's Guacamole.
For the Lazy Girl's Guacamole:
Mash avocados and garlic salt to desired consistency. Taste and adjust garlic salt if necessary.
Notes
If you choose to make each component ahead of time, they do not need to be warmed back up before assembling then making the quesadillas.
Estimated nutritional information does not include guacamole.