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Heat oven to 300°F (150°C). Cover 1 to 2 baking sheets with parchment paper or a nonstick baking mat.
Cut each small tomato in half lengthwise and arrange cut side up in a single layer on prepared sheets.
Drizzle lightly with olive oil and sprinkle with salt. Bake in oven for approximately 90 minutes, until somewhat shriveled and dry to the touch, but not fully dehydrated. Set aside until needed, letting them cool.
Roughly chop the garlic on a cutting board, then add oregano, salt and a few grinds of black pepper. Mince the mixture with your knife until it’s a grainy herb paste.
Transfer to a small bowl, whisk in lemon juice and vinegar, then slowly drizzle in oil, whisking the whole time. Taste and adjust as needed.
In a giant bowl, place drained pasta, roasted tomatoes, cheese, pine nuts and olives and toss gently to combine.
Add dressing to taste, along with any extra salt and pepper needed. Finish with basil.