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 (400F) 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 the oven (400F) for 20-30 minutes or until you need them.
Preheat your main pot over mediumish heat along with a glug of oil. Add the ground beef and give it a good salting (I used a heaping teaspoon). Cook until fully browned, stirring regularly. Once cooked you can set the beef aside and optionally drain some fat from the pan.
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.
Add the ground beef back to the pan along with: 1.5 tablespoons Mexican oregano, 1/2 teaspoon cumin, and some freshly cracked black pepper. You can let this simmer as you work on the chile puree. If it gets to a point where you feel like it's overcooking, simply remove it from the heat until you're done with 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 then 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 two chipotles in adobo (optional). I usually cut off the stem and scrape out the seeds of the chipotles. 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. For milder batches you can blend without any chipotles to start with -- to increase the heat simply blend in 1/2 chipotle at a time and taste test along the way.
Add the chile puree to the beef mixture and cook briefly over medium heat.
Add the remaining roasted tomatoes to the pan and give 'em a rough chop. Add the remaining 4 cups of stock to the pan. I usually add the stock to the blender and swish it around to get any remaining puree before adding it to the pan. You can also add the beans at this point. I used 2 cans of black beans, drained and rinsed, 15 oz. size.
Bring everything up to temp and take a final taste for seasoning. I added another pinch of Mexican oregano, some adobo sauce from the can of chipotles, and another generous pinch of salt. Keep in mind the exact salt level will depend on which stock you're using.
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 Masa Harina or cornstarch slurry. I added 3 tablespoons of Masa Harina to a small bowl and combined it with 4-5 tablespoons or cold water. Once combined add this mixture to the Chili, stirring well, and it will thicken up noticeably.
Serve immediately. I served it up plain Jane in a bowl, but you could also top with your choice fixings: Crema, freshly chopped cilantro, cripsy tortilla strips, or a squeeze of lime.
You can optionally make a cheese quesadilla for dipping. Simply add cheese to half of a flour tortilla in a dry skillet over medium heat. Fold the tortilla in half and cook each side until lightly browned.
Store leftover Chili con Carne in an airtight container in the fridge where it will keep for a few days. To reheat I usually give it a few minutes in a covered saucepan over medium heat -- if it seems thick I'll just add a splash of water or stock to thin it out.