Heat the oil in a large nonstick skillet over medium-high heat. Add the tomato paste, chili powder, cumin and cayenne and cook, stirring, until the oil is brick-red and the mixture is dry, about 2 minutes. Add the ground turkey and 1 teaspoon salt and cook, stirring and breaking up into smaller pieces, until the mixture is combined (the turkey doesn't need to be cooked all the way through at this point). Transfer the mixture to the insert of a 6-quart slow cooker.
Add the tomatoes, chicken broth, cocoa powder, vinegar, oregano and 1 teaspoon salt to the skillet over medium-high heat and bring to a simmer, whisking. Cook for about 2 minutes. Add the tomato mixture, beans, onions, crushed tortilla chips and garlic to the insert and give the mixture a good stir. Cover and cook on low for 6 to 8 hours.
Add chicken broth to thin the chilli, if necessary. Season with salt. Serve with scallions, Cheddar, sour cream, pickled jalapeno and tortilla chips.
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