Preheat oven to 400 degrees. Toss butternut squash with 2 tablespoons olive oil, salt and pepper. Bake 15-20 minutes or until softened.
Unwrap chorizo and break apart in hot skillet. Cook chorizo until the texture starts to resemble ground beef. {It will be softer then that, fyi.}
Remove chorizo to paper towel lined bowl and set aside. If there's a lot of extra grease from the chorizo, wipe out pan.
Saute onions in same pan with remaining 1 tablespoon olive oil. Once onions start to soften, stir in garlic and cook another 2 minutes. Stir in cooked chorizo, roasted butternut squash, beans and cumin. Set aside.
To assemble quesadillas, preheat large skillet over medium heat. Melt 1/2 tablespoon butter and place tortilla into pan.
Top with cheese, filling, slices of tomato and more cheese. Finish with another tortilla. Flip once tortilla has browned. Brown other side of quesadilla and remove from heat. Stand 3 minutes and slice into wedges. Serve with sour cream, salsa and guacamole.