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Combine the white wine vinegar, water, sugar, and 1 tsp kosher salt in a small saucepan over medium heat, stirring until the sugar and salt dissolve, about 2 minutes. Remove from heat, add the sliced jalapeños, and let them sit in the brine for at least 30 minutes at room temperature until slightly softened and tangy. (The jalapeños can be made up to 1 week ahead and stored in the refrigerator.)
Whisk together the lime juice, olive oil, minced garlic, cumin, smoked paprika, chili powder, 1/2 tsp kosher salt, and black pepper in a large mixing bowl. Add the skirt steak portions and turn to coat thoroughly. Marinate at room temperature for 20–30 minutes, or cover and refrigerate for up to 4 hours.
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