Step 1Soak the chipotle pepper in just enough warm water to cover (weigh the chipotle pepper down with a heavy spoon or other utensil to keep it submerged).
Step 2Heat a 2-quart heavy-bottomed saucepan over medium-low heat. Add 2 tablespoons grapeseed oil and the onion and cook, stirring occasionally, until the onion begins to wilt and soften, about 10 minutes. Continue cooking until the onion slowly begins to collapse and caramelize, stirring more frequently. Cook until the onion is almost jam-like in consistency and is a rich golden-brown, about 45 minutes. Remove the caramelized onions. You will use 2 tablespoons caramelized onions for the remainder of this recipe; the rest of the caramelized onions can be used in other recipes and will keep, covered and refrigerated, up to 1 week.
Step 3Add the remaining tablespoon grapeseed oil to the pan (enough to coat the bottom of the pan) and stir in the celery, carrots and fennel. Cook over low heat until the vegetables are well caramelized but not brown. They should have a slight golden color and should not be completely dry. This process should take 20 to 30 minutes over low heat.
Step 4Stir in the 2 tablespoons caramelized onions. Add the smashed garlic clove and the oregano, and stir until the garlic is fragrant, about a minute.
Step 5Increase the heat slightly and add the diced tomatoes and the chipotle with its water, scraping up any bits of caramelized flavoring from the bottom of the pan. Adjust the heat to a simmer and cook the vegetable mixture for 30 minutes. Remove from heat and set the soup aside to cool. Taste the soup and discard the chipotle if desired before blending to minimize the heat.
Step 6Blend the soup using a blender or food mill, then strain. The soup will be very thin but should be very flavorful.
Step 7Season with three-fourths teaspoon salt and one-fourth teaspoon pepper, or to taste. If making the soup ahead of time, make sure it is completely cool, then refrigerate or freeze it until needed.
Step 8Before serving, gently heat the soup and whisk in 1 pint of the cream and paprika. Adjust the seasoning to taste. This makes a scant 3 quarts soup.
Step 9In a small bowl, whisk together the fresh goat cheese, one-fourth cup cream and one-half teaspoon pepper until it has a whipped cream-like consistency. Dollop the chevre mixture onto the hot soup. Drizzle over some extra virgin olive oil as an extra garnish before serving.