Milenas Roasted Tomato Soup

Ingredients

• 4 1/2 pounds tomatoes (a mix of heirlooms, beefsteak and plum tomatoes)
• 3 garlic cloves, unpeeled
• 1 to 2 slices butternut squash (optional)
• -- About 2 teaspoons light brown sugar, if using squash
• -- Olive oil
• 2 tablespoons balsamic vinegar
• -- Kosher salt
• -- Freshly ground black pepper
• 1 tablespoon light brown sugar, if using squash
• 1 tablespoon butter
• 1 1/2 cups roughly chopped onion
• -- Up to 2 cups water for thinning soup
• 4 tablespoons minced fresh basil + more to taste
• 1/2 cup half-and-half (optional)
• -- Additional half-and-half or creme fraiche and basil leaves, for garnish (optional)

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