Wipe off any dusty crevasses on the dried chiles. De-stem and de-seed the chiles, but don't worry about getting rid of every last seed. Roast them in the oven for 1-2 minutes or until warm and fragrant. Add the roasted chile pieces to a bowl and cover them with the hottest tap water you've got. Let them reconstitute for 20 minutes or so.
Rinse and de-stem the tomatoes. Roast them in a 400F oven for 20-30 minutes or until you need them.
Preheat your main pot over medium-high heat along with a glug of oil. Chop up the chuck roast into 1-1.5" chunks and give it a good salting. You can discard any fat pieces that you don't want in your Chili. Sear the beef chunks in the pot until they are browning on all sides (tongs work great for this step). Once browned you can set the beef pieces aside.
In the same pot, add a finely chopped onion along with another glug of oil. Cook the onion over medium heat until softened. Then add 4 minced garlic cloves and briefly cook. Scoop half of the onion-garlic mixture into the blender where it will become part of the chile puree. Note: if you're concerned about the garlic burning then add the 4 cups of stock to the main pot now while you work on the chile puree.
Before draining the reconstituted chiles take a taste of the soaking liquid. If it tastes bitter to you then use stock to combine the chiles. If you like the flavor you are welcome to use the soaking liquid in place of the stock.
Add the drained chiles to the blender along with a single roasted tomato and a single chipotle in adobo (optional). I usually cut off the stem and scrape out the seeds of the chipotle. Half of the onion-garlic mixture should already be in the blender. Add a single cup of stock (or soaking liquid) and combine well. Feel free to add a bit more liquid if it won't combine readily.
Add the chile puree to the main pot along with: 1 tablespoon Mexican oregano, 1/2 teaspoon cumin, 1 teaspoon salt, freshly cracked black pepper, and the 4 cups of the stock if you have not already added it. Combine well and then add the seared beef pieces (along with their juices) and the remaining roasted tomatoes. I usually just plop the tomatoes in the pot and give 'em a rough chop.
Bring this up to a simmer, cover, and let cook for 1.5-2 hours or until the beef is tender. This batch cooked for 2 hours. Note: my stove needs somewhere between low and medium-low to maintain a simmer in a covered pot.
Towards the end of the simmer you can add the beans (optional). I added two cans of drained and rinsed black beans, 15 oz. size.
Take a final taste for seasoning. I added more salt and another pinch of Mexican oregano, but keep in mind the salt level will depend on which stock you're using. You can optionally shred the beef chunks into smaller pieces using two forks, or you can just leave them as the larger chunks.
You can also adjust the consistency of the Chili at this point if you want. To thin it out, simply add 1-2 cups of stock. To thicken it up you can use a cornstarch slurry. In a small bowl whisk together a few tablespoons of cornstarch and equal parts cold water. Once combined add the mixture to the Chili and it will thicken up considerably. More on using cornstarch to thicken soups and sauces.
Serve immediately. I served this batch plain Jane, but optional garnishes include Mexican Crema, freshly chopped cilantro, crispy tortilla strips, and a squeeze of lime.
Store leftovers in an airtight container in the fridge where it will keep for a few days.