Prepare Chiles
Soak chiles in near-boiling water for 30 minutes.
Sear Beef
Season chuck roast with salt and pepper.
Heat 1 tablespoon oil. Sear roast in batches until browned. Set aside.
Build Braising Liquid
Add remaining oil, tomatoes, onion, and garlic. Cook 2-3 minutes.
Deglaze with beef broth.
Add hydrated chiles, short ribs, spices, and cinnamon stick. Boil, then simmer 30 minutes.
Remove short ribs and cinnamon stick. Skim impurities from liquid. Reserve 1.5-2 cups liquid, cover, and refrigerate.
Blend remaining chile and tomato mixture until smooth.
Return short ribs, seared beef, and juices to pot. Add orange juice, apple cider vinegar, salt, and pepper. Simmer, cover, and cook 3-4 hours.
Finish and Assemble
Remove short rib bones. Shred all meat.
Dip tortillas in reserved braising liquid.
Place tortilla on skillet. Top with cheese, shredded beef, onion, and cilantro. Fold.
Cook 30-45 seconds per side until crisp.
Repeat with remaining tortillas. Serve with dipping liquid and lime wedges.
