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I have always done the cut side up. Also, scoop out the insides because the tomato 'water' has no flavor and only slows down the process. Consider a sprinkle of Italian seasoning.
Hmmmmm. I have always done cut side down in a hot oven, peeled them and used whatever juices are in the pan in the soup. I think the juices are very flavorful.
I've roasted roma (plum) tomatoes whole, with a light drizzle of olive oil and a few whole cloves of garlic, in a 325-degree oven for about 2 hours. As they cook, the skins split; you can lift them right out. I keep the juices, mash the tomatoes a bit, and use the results as a base tomato sauce for soup or sauces. If you want a smoky flavor, I'd roast them at a much higher heat for a shorter amount of time.
I made this recipe last night, exactly as written (cut side down) and the skins blistered up nicely in the oven and slid right off when I pinched them over a bowl. It was so easy and the soup is DELICIOUS!
Also, as I couldn't get beefsteak tomatoes here in Bangkok, I used smaller ones and more of them so my cooking time was only 45 minutes. Still worked great and you want all that watery pulp to make it more like soup and less like sauce so I wouldn't scoop the middles out before roasting.