Preheat the oven to 500 degrees while you line a baking sheet with parchment paper. Drain the tomatoes in a fine mesh strainer and set over bowl; pressing to help extract any extra juices. Reserve 1 3/4 cups of strained juices then whisk in the date sugar and lime juice; set aside for later.
Combine the onion, chilis, 2 tbsp of olive oil, 2 3/4 tbsp of chili powder, garlic, 1/2 tsp salt, and drained tomatoes into a second bowl. Transfer the tomato-onion mixture to the prepared baking sheet in an even layer and roast until charred for about 35 minutes. Toss mixture halfway through cooking time to help with even roasting.
Spread the tofu onto paper towels and let drain for about 20 minutes to remove any extra moisture then coat in remaining chili powder, salt, and pepper.
Heat remaining olive oil in a large skillet over medium high heat then cook the tofu for about 3 minutes per side until golden brown. Place cooked pieces on paper towels to drain off any excess oil.
Transfer roasted tomato mixture to now empty skillet and stir in reserved tomato-lime juice mixture. Nestle the tofu in the sauce then bring heat up to medium and cover for about 2 minutes.
Remove from the heat, sprinkle with the avocado, cilantro, and scallions. Serve with warmed corn tortillas and enjoy.