First, get the butternut squash in the oven. Preheat oven to 400 degrees Fahrenheit. Add butternut squash to a large bowl and toss with olive oil. Sprinkle with cumin, paprika, salt, and pepper and toss again until well-coated. Spread on a large rimmed baking sheet - I like to line mine with parchment paper for easier clean-up. Bake, stirring once or twice, until tender and some sides are golden brown, about 25 minutes.
While the squash roasts, start the soup. Set a medium soup pot over medium-low heat. Add the olive oil. When hot, add the onion. Cook, stirring occasionally, until the onion is soft and just beginning to brown, about 8 minutes. Add garlic, cumin, cinnamon, cayenne, 1/2 teaspoon kosher salt, and 1/4 teaspoon black pepper and cook, stirring constantly, for one minute.
Add the vegetable broth and 2 cans (3 cups) of the drained black beans. Stir well and remove from heat.
When the squash is cooked, add half the squash to the soup. Working in batches with a blender or using an immersion blender, puree the soup. Return the soup to the stovetop and add the remaining can (1 1/2 cups) beans and all but 1/2 cup of the remaining butternut squash. Stir and cook over medium low until hot.
Add red wine vinegar and stir to combine. Taste and add more salt, pepper, and/or cayenne if desired.
Serve with assorted toppings and reserved roasted butternut squash.