For chili - “a bowl of red” - chipotle, dried or not, is generally just an accent. The chile most commonly used are dried pasilla and/or ancho and/or California and/or New Mexico, often in combination with fresh green chile like poblano and/or “long green”. Many of these name might vary by region, BTW. The general approach with dried is to de-seed, toast lightly, soak, and then blend to a paste. Fresh chile is often roasted to remove skin, de-seed, and blend. Recipes are dime-a-dozen if you spend 2 minutes googling. But you might have to do more research if you want to understand regional differences. Chile is not chile and chili is not chili. Nor is chile chili or chili chile.
To post 3, add guajillo pepper as one of the best dried pepper to use for the base flavor of your chile. A very bright chile flavor. I don’t know why my finger didn’t type that earlier.
I have used dried chipotle, both ground and flaked, in chili many times, though always as brianshaw said, as an accent rather than as a replacement for more conventional chile powder. I like the hint of smokiness it brings to the party. If I don't have any fresh jalapeños on hand I'll sometimes add a bit more chipotle as a replacement, but still use primarily either conventional chile powder or, if I'm feeling ambitious, my own chile paste or dried ground mix.
I love my whole chili pepper chili. I bet if you had really good, really fresh powder, there wouldn't be much difference, but I bet that's uncommon. I use mostly ancho (three or four, lazily seeded, for three pounds of beef), a fresh jalapeno, and a fresh green chili if I can find it. I also started adding chipotle chili powder as part of a DIY blend because I found some beautiful fresh stuff. I think chilies are like spices when it comes to pre-ground. I'm sure there are good powders out there, but I haven't tasted one that brings the jammy fruit flavors of whole dried ancho.
Next time I make chili, I plan on putting in some smoked, dried moritas. A friend of mine gave me about an oz. I can't wait to use it,.
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