Preheat oven to 400°F.
In a saucepot, combine dried chilies and stock, and simmer at a low boil for 45 minutes. Add to a food processor and reserve.
Sauté onion in olive oil with the garlic, oregano, salt and pepper until softened, 10 minutes. Add beer, reduce to 1/2 cup, add to food processor along with tomato sauce or purée and process chili sauce. Pour back into the saucepot and reserve.
On a parchment-lined baking sheet, dress butternut squash with cooking spray, spices, salt and pepper. Roast until tender and browned at edges.
Heat a skillet over medium-high heat. Add olive oil, 1 turn of the pan, and onion, garlic, jalapeño, cumin and salt. Cook to tender; add black beans and wilt kale into the pan. Stir in hot sauce. Add roasted squash to the black bean and kale mixture.
Char and blister the tortillas over an open flame on a gas burner or in a hot, dry, stainless skillet over high heat on an electric stove.
Dip a side of each tortilla in the chili sauce. Top sauced side with the veggie filling and some cheese. Roll up tortilla and place in a casserole dish. Repeat with remaining tortillas and filling. Top enchiladas with remaining sauce and cover with remaining cheese, about 2 cups.
Bake enchiladas to golden on top, 20-25 minutes. Garnish with pickled red onions, pepitas and cilantro, and serve.