Preheat oven to 400°F. Bring a kettle of water to a boil.
Place 3/4 cup couscous in a small bowl with a pinch of salt and a drizzle of olive oil. Pour 2/3 cup boiling water over the couscous, stirring to combine. Cover the bowl with plastic wrap and set aside.
Bring 2 cups of water to a boil in a medium saucepan. Add a pinch of salt and 1 cup of Israeli couscous. Simmer until al dente (soft on the outside, some bite left on the inside, about 16 - 18 minutes). Drain the Israel couscous then rinse under cold running water. Let dry then add to a large bowl. Fluff regular couscous with a fork then add to the same bowl.
Spread yellow cherry tomatoes out on a baking sheet and drizzle with a little olive oil. Sprinkle with kosher salt and black pepper then roast for 12 -13 minutes. The tomatoes will start to collapse and turn golden brown. Set aside to cool.
To the bowl with the couscous, add roasted yellow tomatoes, orange tomato wedges, halved red cherry tomatoes, sliced sun-dried tomatoes, oregano, tarragon and mint.
Prepare the vinaigrette by placing minced sun-dried tomatoes, both vinegars, garlic and olive oil in a mason jar. Season with a pinch of kosher salt and several turns of black pepper. Lid the jar and shake until well-combined.
Spoon some of the vinaigrette over the salad then gently toss to combine. I didn't use all of the vinaigrette. Season to taste with additional kosher salt and freshly ground black pepper.