Combine the onion, 2 tablespoons of the vinegar and 1/4 teaspoon salt in a small bowl and toss to coat; set aside.
Combine the coleslaw, pickles, 3 tablespoons of the vinegar and 1/4 teaspoon salt in a medium bowl and toss to coat; set aside.
Heat the oil in a large nonstick skillet over medium-high heat. Add the beef and cook, stirring frequently, until beginning to brown, about 4 minutes. Stir in the taco seasoning and 1/2 teaspoon salt and continue to cook until the meat is cooked through, 2 minutes more. Reduce the heat to low, stir in the ketchup, sugar, 1/2 cup water and remaining 1 tablespoon vinegar and simmer, stirring occasionally, until the sauce is slightly thickened, about 8 minutes.
Meanwhile, put the tortilla bowls on a baking sheet and sprinkle with the pepper jack. Bake until the pepper jack is melted and the tortilla bowls are slightly golden in spots, about 5 minutes.
Drain the liquid from both the coleslaw and onions. Divide the meat among the tortilla bowls and top with the coleslaw and onions.
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