Preheat a griddle pan for the grilled cheese over medium heat.
Heat a medium soup pot over medium-high heat, add the olive oil and melt 2 tablespoons butter into the oil. Add the garlic, onions, chipotle, adobo sauce and some salt and pepper. Partially cover the pot and cook to soften, 10 minutes or so. Stir in the tomato paste and cook until fragrant, 2 minutes, then deglaze the pan with 2 cups of the chicken stock and transfer to a food processor. Add the tomatoes and process until smooth. Pour the soup back into pot and add the remainder of stock. Simmer at a low bubble while you make the grilled cheese.
Lightly butter 1 side of the bread slices. Make the cheese sandwiches with, and grill until crispy and the cheese melts.
Stir the sour cream into the tomato soup and serve in shallow bowls with chives to garnish, and grilled cheese on the side for dipping.
When blending hot liquid, first let it cool for five minutes or so, then transfer it to a blender, filling only halfway. Put the lid on, leaving one corner open. Cover the lid with a kitchen towel to catch splatters, and pulse until smooth.