The reason you cook them separately is because beans can cook at different times, and you want them all to hold up at the end. If you don't have the time or patience for it, tinned beans are fine, but the flavour won't be as developed. Get them cooking until they're a little short of being done to tenderness. They're going to cook all together to complete the cooking.
First and foremost, chili isn't chili without smoky flavour. Some people use spices (smoked paprika, toasted cumin, toasted coriander, liquid smoke, vegan Worcestershire, etc.), while others roast off some veggies and peppers low and slow in the oven to impart that smokiness, while still others actually go through the process of smoking their veggies. We can't do the actual smoking here at Chow, and we don't use liquid smoke (there's some sort of chemical in there that Boss Man doesn't jive with), so instead, we rely on the spices and the oven.
For one thing, we don't put raw chiles in there. We roast them in the oven on a parchment lined baking sheet for about 30 - 45 minutes at 350ºF until the skins are blackened through, and will peel easily. Seeing as how we don't want our patrons to be in pain, we remove the seeds, but at home, I leave the seeds in. Then, we roast off some red peppers. It takes a little longer for roasting red peppers, but the wait is definitely worth it.
While you're there, consider using a pair of gloves when peeling the chiles. I've been handling them all my life, so it doesn't bother my hands, but one of my coworkers in the kitchen said, "Are you sure you don't want gloves?" I looked confused until he explained that for a lot of people, the chiles are really hot in the mouth and on the hands. If this is the case for you (that is, you don't handle very hot chiles with your bare hands on a regular basis), then please get yourself some gloves, and protect your hands.
If you're actually not a fan of heat at all, go ahead and use some sweet peppers, so that you still get that smoky aroma without the heat at all. The bell peppers can only take you so far, after all. Anyrate, once all the peppers are roasted, go ahead and pop them into a plastic bag, and close the bag tightly. I use a zip top bag, which works just fine for my needs, because I can dump all the used skins right into that bag, and not make a mess. Once they've sat in the bag for a goodly 20 minutes or so, the skin should come off quite easily.
While you wait on the peppers to roast (and then, subsequently, to peel), go ahead and start chopping your onions, garlic, celery, carrots, (standard mire poix, with a bit of a garlicky punch; it's lovely). Don't worry too terribly much about everything being perfect and tiny sized. This is chili, not some fancy frou frou thing that's fussy or finicky. I like corn in mine, and I know some people who like theirs with a couple of extra vegetables. Whatever you fancy, go with it. Since corn is out of season, Boss Man isn't about to add it, so we're talking beans, more beans, and a bit of TVP for texture contrast.
Once the veggies are chopped, sautee them slowly over medium high heat, along with your favourite spices. The closest that I've managed to get at home that's like Boss Man's spice blend is garam masala or chinese 5 spice mixed in equal parts with chili powder (the kind with ground chile, garlic, and a bunch of other spices, not the kind that's just ground red chile), and finished off with a bit of dark chocolate at the end, but you may have your own that you like to use. Once the veggies have come together, stir in some tomato paste, diced tomato, alcohol of your choice (stick to tequila or vodka if you're gluten free; otherwise use beer) your dried herbs of choice (I like thyme and oregano, myself, but you can use your favourites, like sage or rosemary), and salt to taste. You want to add the herbs at this stage, because you want their flavours to draw out slowly into the surrounding liquid. Simmer this mixture for a good 30 minutes or so, over lowest heat, covered. You can add a bit of water if the mixture looks too dry. You're looking for a thick gravy consistency.
By now, the beans should be almost completely cooked through, the peppers and chiles should be seeded, skinned and chopped, and your tomato/spice mixture should be smelling quite tempting and lovely. At this point, you have a couple of options. The first is to drain the beans of the cooking liquid, and tip them into the tomato mixture, add in about 4 cups of liquid (stock, wine, or water), and cook together for about 35 minutes over a low bubbling simmer. The other option is what you'd do if you're going to add some TVP or tofu to the chili to give it a textural contrast. Tip in the beans, with their cooking liquid into the tomato/spice pot. Add the roasted peppers, the roasted chiles, ,and taste for salt. If it's a little bland, don't worry. It'll intensify as the chili cooks down. Allow the beans and the rest to simmer slowly for 35 minutes (at least). This will evaporate any excess liquid and let the beans get done to tenderness. If you added the beans with their cooking liquid, throw in some TVP or thawed tofu to bulk it up and give it texture. This will take care of any excess liquid you've got. In the last 10 minutes of cooking, add your garlic, chocolate, and adjust the salt as needed.
If you could use a bit more heat, add a bit of cayenne. If it's too hot for your liking, add a bit of fruit juice (apple works great). To finish it, garnish with piles of cilantro, basil, or scallions, and serve with fat wedges of limes. When something has been simmering that long, you'll want some acid to brighten the flavours. At Chow, Boss Man adds the acid at the very end, so that when people want a bowl of chili, all they have to do is ask for it, and it appears. But at home, you can add those little touches to make it lovely and comforting.
There's a couple of reasons why this is the ideal, perfect winter/autumn dish. For one thing, it's got heating spices (such as the cumin, the cinnamon, etc.; if you use garam masala, the whole entire thing is made up of heating spices) and heating veg (the bell peppers and the chiles). In Indian medicine, those heating spices help warm the blood, and keep your circulation going. They're quite tasty, and good for you at the same time. Furthermore, cumin helps prevent excess gas accumulation. And if I know anything about vegans, this is a very important thing.
Of course, the beans and TVP/Tofu itself is loaded with protein. The tomato and peppers (especially if you're using red peppers) are loaded with vitamin C. And, since it's all plant food, you've got lots of fibre in there, which fills you up, and keeps you full for a good long while. Nothing can stop you when you're running on plant power!
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