Cook the bacon in a cast-iron Dutch oven over medium-high for 5 minutes. Add the butter, sage, rosemary, shallots and a pinch of salt, and cook an additional 5 minutes, stirring occasionally.
Meanwhile, cut off the skinny neck of the squash and cut in half (remove the stem, but leave unpeeled). Cut the bulb into 4 quarters. Remove the seeds and stringy flesh and add them to the Dutch oven. Cook until fragrant and golden, about 5 minutes. Deglaze the pan with the white wine and allow to reduce for a couple of minutes. The seed mixture should look rich and flavorful. Add 2 cups water and the chicken stock and nestle in the squash, flesh-side up (you should be able to just fit one nice-size squash in almost one layer). Cover and simmer until very tender, about 40 minutes.
Once cooked, cool slightly, remove the squash, scoop out the flesh and place in powerful blender. Strain the liquid through a metal sieve, gently pressing against the solids to extract all of the flavor. Blend the broth with the squash until very creamy, about 1 solid minute on high. Wipe the Dutch oven clean and place the soup back into the pan. Heat gently, and then stir in the vanilla just before serving. Season with salt and pepper and pour over a little chunk of either cooked spicy sausage or a small lump of crab meat in a shooter glass. Top each shooter with a tiny bit of chopped chives.
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