Pre-heat oven to 400°F. Line a large baking sheet with parchment paper and spray the parchment with an even layer of cooking spray.

Place the cubed butternut squash on a baking sheet and drizzle with olive oil.  Roast at for 1 hour and 15 minutes, flipping the squash half-way through.

Cut the onions into thin slices and set aside. Shred the manchego cheese, and refrigerate until ready to use. Let the goat cheese sit out at room temperature.

Heat 2 tsp. of olive oil in a skillet over medium heat.  Add the onions, and granulated sugar. Saute for 6-7 minutes, tossing every few seconds. Onions will start to brown and become tender. You want the onions to be soft, but you don't want them to burn so be sure to watch them closely. Once they start to brown, add the balsamic vinegar and let cook for another 1-2 minutes. Remove from the pan and set aside.

Remove squash from the oven and transfer to a food processor bowl. Add butter, brown sugar, nutmeg, salt and pepper and pulse for 1 minute until smooth. If you don't have a food processor, a potato masher works fine.

Place tortillas on a work surface. Spread a generous layer of goat cheese on each tortilla. Add a layer of  squash, caramelized onions and shredded manchego cheese, and fold each tortilla in half.

Spray a clean cast iron or non-stick skillet with a light coating of cooking spray and grill each quesadilla over medium heat for 1-2 minutes on each side. You want the cheese to be melted and tortillas to be golden brown.

Transfer quesadillas to a cutting board, cut into thirds and serve.