Preheat smoker to 180 degrees. Pat dry beef chuck roast, then rub down with adobo sauce. Mix together the ancho chili powder, kosher salt, cumin, smoked paprika, chili powder, pepper, and cinnamon. Coat the beef roast with the seasoning in a thick layer, then smoke for 3 hours.
Remove roast from smoker and turn the heat up to 275 degrees. Place roast in a large, oven-proof Dutch oven and add the chipotle chiles, garlic, onion, and crushed tomatoes. Cover with the lid and place back into the smoker for 5 hours, or until the meat is fork-tender and falls apart with a light touch. Remove from smoker and let sit for 15 minutes before removing from the Dutch oven and shredding. Ladle a little of the sauce onto the shredded meat if desired for extra heat.
While the meat is cooking, prepare the pico by combining all the ingredients in a large bowl and tossing gently to combine. Keep covered in the fridge until ready to serve.
To serve, add meat to a tortilla, then top with pineapple pico and slices of avocado. Enjoy!