Preheat oven to 400 degrees, 375 if you are using a convection oven
Prep your baking sheets (sheet pans) by either brushing them lightly with olive oil or lining the pans with parchment paper. Both will keep the tomato skins from sticking to your pans. The paper will make for quicker cleanup.
Cut the stems off the tomatoes and slice them in half. See the photos for how your tomatoes should look with the stems removed. Place the tomatoes skin side down on the pans and use the 1/3 cup olive oil to brush or drizzle the olive oil on the tomatoes.
Roast the Tomatoes for 20 minutes if you are using a convection oven and 28 minutes if using a regular oven, or until they have darkened and softened. You can refer to the photos for how they should look coming out of the oven.
While the tomatoes are roasting, prep the rest of your ingredients. Let your chopped onions and garlic sit for a good 10 minutes before adding them to the hot oil. This will enhance and preserve their flavor and health benefits.
Coat the bottom of your pan with the remaining 2 Tbs of olive oil. Heating your pan on medium, add your onions, sweating them until they are translucent, about 5 minutes.
Add the roasted tomatoes, garlic, herbs, salt, pepper and broth, cooking for 20 minutes.
Blend the soup mixture using an immersion blender, standing blender, or food processor. Whatever you have handy.
Return the soup to the pot. Add the Red Wine Vinegar and heat for 10 more minutes. Soups Done! Grab some crusty bread and dig in.