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Preheat oven to 375°F. Place a wire rack on a rimmed baking sheet. Arrange the tomatoes, vines intact, on the rack. Brush with 2 tablespoons of the olive oil and season with the salt and pepper. Roast for 30-45 minutes, Remove from the oven and let cool.
Turn on an indoor grill pan on medium-high heat. Cut avocado in half, remove pit with a spoon then cut into quarters with skin intact the whole time. Drizzle with juice from half of a lemon and brush lightly with 2 tablespoons of olive oil, Gently place cut-side down on grill for 2-3 minutes, make sure to grill on both exposed sides. Pull from grill and let cool. Once cool, remove peel and set avocados in the fridge until ready to assemble.