Preheat comal to medium high, then add the roma tomatoes, serrano pepper, and garlic cloves to the dry skillet and let char until blackened, turning occasionally, around 5 minutes. Add to a blender and pulse until smooth. Season with salt as necessary. Set aside
Preheat oven to 400 degrees. Cut the puff pastry into four large circles, roughly 4-5 inches in diameter. Leaving a ¼ inch border, score the puff pastry, then prick the middle with a fork. Place on a parchment lined baking sheet and bake for 10 minutes.
Press down the middles of each puff pastry round if needed, then divide the monterey jack cheese between the rounds. Crack one egg into each hole, then place back in the oven for 10-15 minutes or until the egg whites have set. Top each egg in a hole with diced tomato, avocado, cotija cheese and 1 tablespoon of the chile. Sprinkle with salt and pepper and serve immediately.