This took a bit of time, but no real effort. It is hard to give exact measurements as so much depends on how moist the tomatoes are, etc. I'll give you a general idea of what I used, but you really will need to taste and adjust as you go along. Soup ain't an exact science, 'ya know?
About 4 pounds tomatoes, quartered (I used Black Crimeans and Brandywines)
6 large garlic cloves
1/4 cup olive oil (you will need more later)
Salt/Pepper
6 small Yukon Gold potatoes, diced very small
4 tablespoons unsalted butter
2 tablespoons olive oil
1 teaspoon dried thyme
2 teaspoons dried rosemary
2 cups rich vegetable broth
1/2 cup finely grated Parmesan cheese
2 tablespoons sweet paprika (not smoked)
Extra olive oil, if needed
Heavy cream for garnish
Heat the oven to 350 degrees F. Cut the tomatoes and place in a deep casserole and toss with olive oil, garlic cloves and a bit of salt and pepper. Roast until soft-about an hour.
While tomatoes roast, cook the potatoes in the butter and olive oil with the thyme and rosemary until quite soft. Do this over medium heat. If they brown, it isn't a big deal, but better to keep an eye on them so they do not burn. You don't want burnt.
Combine tomatoes and potatoes and cook over medium heat until liquid reduces by 1/4.
Cool slightly then carefully puree in batches in a blender. Be sure to let the hot air out every so often (just take my experienced word for it). Return to pan, add paprika and cook again until reduced by about 1/4 and then add the broth. Cook until thickened to your liking. Stir in the grated cheese until melted. At this point, taste for seasoning adjustments. I often find soup needs another drizzle of olive oil at the end, particularly if the tomatoes are very bright.
Before serving, swirl some heavy cream on top.
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