Begin by preparing the marinade for the flank steak. In a mixing bowl, combine ½ cup of olive oil, chili powder, cumin, brown sugar, smoked paprika, chipotle chili powder, onion powder, garlic powder, lime juice, minced chipotle chili, and a pinch of salt and pepper. Whisk everything together until well combined. Place the flank steak in a resealable bag or shallow dish and pour the marinade over it, ensuring the steak is well coated. Seal and refrigerate for at least 30 minutes, or ideally, a few hours to allow the flavors to infuse.
Preheat your oven to 400°F (200°C). While the steak is marinating, prepare the potatoes. Scrub them clean and pierce each potato several times with a fork. This step helps steam escape during baking, preventing explosions! Place the potatoes directly on the oven rack or on a baking sheet lined with foil. Bake for about 45-60 minutes, or until they are tender when pierced with a fork.
While the potatoes are baking, heat 3 tablespoons of olive oil in a large skillet over medium heat. Add the sliced red and orange peppers, seasoning them with a pinch of salt and pepper. Sauté for about 5-7 minutes until they are soft and slightly caramelized. Remove from heat and set aside.
Once the potatoes are nearly done, remove the steak from the marinade and shake off any excess. Heat a grill pan over high heat (or grill) and cook the steak for about 4-5 minutes on each side, depending on your preferred level of doneness. For medium-rare, aim for an internal temperature of 130°F (54°C). Once done, let the steak rest for a few minutes before slicing it into thin strips.
In a blender or food processor, combine the ripe avocado, Greek yogurt, lime juice, adobo sauce, and a pinch of salt and pepper. Blend until smooth and creamy. Adjust the seasoning according to your taste. If you want a thinner consistency, add a splash of water or more lime juice.
Once the baked potatoes are done, allow them to cool slightly before slicing them in half lengthwise. Use a fork to fluff the insides of each potato. Divide the sautéed peppers and sliced steak among the potato halves. Top each stuffed potato with shredded sharp cheddar cheese and crumbled cotija cheese. Drizzle generously with the creamy avocado chipotle sauce and sprinkle with crushed tortilla chips for added crunch.
Arrange the stuffed potatoes on a serving platter or individual plates. Garnish with additional cilantro, lime wedges, or any other toppings you enjoy. Gather your friends and family around the table, and prepare for a flavor explosion that will have them coming back for seconds!