Preheat the oven to 425 degrees F. Toss the broccoli and tomatoes with the vegetable oil, 1/2 teaspoon chili powder, 1/4 teaspoon salt and a few grinds of pepper on a rimmed baking sheet. Roast, stirring occasionally, until tender, about 25 minutes.
Meanwhile, coat a nonstick skillet with cooking spray and heat over medium-high heat. Add the beef and the remaining 1 teaspoon chili powder; season with salt and pepper. Cook, breaking up the meat, until browned, about 4 minutes. Stir in 1/2 cup enchilada sauce, the beans and 2 tablespoons water. Simmer until the beans are soft, 3 to 5 minutes. Remove from the heat and add the cilantro.
Coat a small baking dish with cooking spray. Divide 1/4 cup cheese and the beef mixture among the tortillas; fold in the sides and roll up. Transfer to the baking dish, seam-side down. Drizzle with the remaining 3/4 cup enchilada sauce and cover with foil. Bake until warmed through, 12 minutes. Uncover, sprinkle with the remaining 1/2 cup cheese and bake until melted, 2 to 3 more minutes. Serve with the vegetables.