Start heating broth in a large/5Qt pot and bring to a boil.
Meanwhile, prepare the squash. Cut squash in half, scoop out the seeds and peel. [Leave the cutting & peeling to adults]. Chop squash into 1" cubes. Place squash in boiling broth and cook for 8 mins (or when squash is soft). When done, strain but save 2 cups of the broth for later.
In a medium pan on medium heat, melt the butter and cook the shallot and garlic for about 5 mins.
In your Vitamix or blender, add squash, 2 cups of the vegetable broth, cooked veggies, sugar, vinegar, and spices. Blend. Put mixture back in the large pot and stir in the cream. Scoop soup into bowls. Serve with crackers or croutons atop, and biscuits on the side.
To save time, buy pre-cut squash.
Squash is done boiling when it is soft in the center. Simply use a fork or pairing knife to assess the squash's tenderness.