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Brown sausage in 1 Tbsp. oil in a skillet over medium-high heat until cooked through. Drain on a paper towel-lined plate; set aside.
Sweat onion and garlic in 1 Tbsp. oil in a large pot over medium heat until soft, 5 minutes. Increase heat to medium-high, add squash and pepper flakes, and saute 5 minutes.
Stir in broth and water, bring to a boil, and simmer until squash is very soft, about 10 minutes. Puree soup with a hand blender (or in batches in a standard blender), then add bell pepper, cream, sage, and sugar; simmer until bell pepper is tender, about 5 minutes. Stir in spinach, brandy, and sausage, and simmer until spinach wilts and sausage is heated through, about 2 minutes; season with salt and pepper.
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