Combine Pasillas and Water: Place the pasillas and 2 cups of water in a bowl. Microwave them until the pasillas are softened, about 3 minutes. After microwaving, do not drain or discard the liquid. The liquid is essential for the next steps as it carries the flavors of the pasillas.
Blend with Tomatoes and Maseca: Add the softened pasillas (with their liquid), tomatoes and their juice, and beef-flavored bouillon to a food processor or blender.
Blend Until Smooth: Process the mixture in the blender until it is smooth, about 1 minute. Once the mixture is smooth, set it aside.
Cook Bacon: In a Dutch oven or a large pot, cook the bacon over medium heat until it's crispy, about 8 minutes. Using a slotted spoon, place the cooked bacon on a paper towel-lined plate and reserve 3 tablespoons of the bacon fat in the pot.
Brown the Meat: Pat beef dry with paper towels and season with 2 teaspoons of kosher salt and 1 teaspoon of ground black pepper. Heat 1 tablespoon of reserved bacon fat in a now-empty Dutch oven over medium-high heat until just smoking—brown half of beef, about 8 minutes. Transfer to bowl and repeat with 1 tablespoon bacon fat and remaining beef.
Layer Flavors: Add the remaining 1 tablespoon of bacon fat, onion, and jalapeño to again-empty the Dutch oven and cook until softened about 5 minutes. Add the garlic and cook until fragrant, about 2 minutes. Stir in cumin, chipotle powder, oregano, coriander, sugar, and cayenne, and cook until fragrant, about 30 seconds. Deglaze the pot by pouring in the beer and let it simmer for 7-8 minutes until it reduces slightly.
Gentle simmer: Stir in the reserved chile-tomato mixture, cooked bacon, reserved browned beef (along with any flavorful liquid from the beef), and the remaining 2 cups of water. Bring the mixture to a boil. Reduce heat to low and simmer, covered, stirring occasionally with a wooden spoon, for 1 hour. Continue to simmer uncovered until meat is tender, 30 to 45 minutes.
Thicken with Masa Harina: In a small bowl, mix Masa Harina with ½ cup of water. Slowly whisk in the mixture into the chili and simmer for an additional 5 to 10 minutes until it slightly thickens—taste and adjust salt and pepper to taste.
Serve: Ladle the chile con carne into bowls and garnish with chopped cilantro, cheese, onion, and lime wedges. Add sour cream if desired for extra creaminess and flavor.