Preheat oven to 450°.
While the oven is preheating, prepare the tomatoes. Add cherry tomatoes to a medium bowl with olive oil. Season with salt and pepper lightly, tossing to coat. Spread the tomatoes in an even layer on a baking sheet lined with a silicone mat or parchment paper. Bake for 10 minutes until tomatoes are softened. Remove from oven and set aside.
Place a 10-inch cast iron skillet in the oven for at least 10 minutes to heat. While the skillet is preheating, prepare the batter.
Blend 2 Tbsp melted butter, eggs, milk, flour, salt, and fresh herbs on high for 30 seconds to 1 minute until the batter is smooth and no clumps of flour remain.
Carefully remove skillet from oven and add 2 Tbsp melted butter to the pan, swirling to coat the pan evenly. Immediately pour the batter into the skillet and place in the center of the oven. Bake for 20 to 25 minutes, until puffed and golden brown on top.
Prepare your remaining toppings while you wait. Remove skillet from the oven when done and top with goat cheese, roasted tomatoes, avocado, red onion, and freshly chopped basil. Serve immediately.