Make the enchilada sauce. Place 1 cup oil in large dutch oven and heat until hot. Add garlic and onions and cook over medium heat for 2 minutes or until onions are soft. Stir in chicken broth, tomatoes with their juices, chili powder, cumin, salt, and pepper. Heat to boiling; reduce heat. Simmer uncovered 1 hour.
Roast butternut squash in roasting pan with 1 tablespoon olive oil, seasoned with salt and pepper to taste for 20 minutes, or until squash is soft and begun to caramelize around the edges. Remove the squash from the oven and stir in the black beans, chopped cilantro, and 1 cup of enchilada sauce.
To prepare the enchiladas, Dip each tortilla into sauce to coat both sides (this is what will make the edges nice and crispy!). Spoon 2 Tablespoons filling onto each tortilla, top with 1 tablespoon cheese. Roll tortilla around filling.
Place seam sides down in ungreased rectangular casserole baking dish (13x9x2 inches). Pour remaining sauce over enchiladas; sprinkle with remaining cheese.
Cook uncovered in 350 degree oven for 15 minutes, or until cheese is melted.