Season steak with cumin, chili powder, garlic powder, onion powder, and salt. Set aside and allow to marinate for about 30 minutes.
Heat 1 tablespoon of oil in a pan over medium-high heat. Saute onion and bell pepper in the hot oil until they are soft, 5 to 7 minutes. Transfer vegetables to a plate.
Preheat the oven to 350 degrees F (175 degrees C). Spray a large baking sheet with cooking spray.
Heat another tablespoon of oil in the same pan over medium-high heat. Saute the steak until no longer pink, 5 to 7 minutes.
Place 6 tortillas on the prepared baking sheet and add a handful of Monterey Jack cheese to each.
Bake in the preheated oven until the cheese melts, 2 to 3 minutes. Remove from the oven and add veggies and meat to each tortilla. Roll up and turn seam side-down. Brush with remaining vegetable oil. Return to the oven and bake until tortillas crisp up, 8 to 10 minutes. Repeat with remaining tortillas.