Make vinaigrette / marinade: Whisk together balsamic vinegar, apple cider vinegar, Dijon mustard, maple syrup, and oil. Season to taste with salt and pepper. (Can be done up to 5 days ahead) 

Marinate kale - Prep kale by tearing leaves off of stems and into bite-sized pieces. Toss with first part of vinaigrette. Cover and refrigerate for at least 30 minutes and up to 1 day. (Can be done 1 day ahead) 

Garlic / Onions / Butternut squash - Prep as directed. (Can be done up to 3 days ahead) 

Bread - Tear into bite-sized pieces. Toss with cooking oil, spread out onto a sheet pan, and lightly sprinkle with some salt and pepper. 

Heat oven to 375F (191C) degrees. Toast bread for 10 to 12 minutes until golden, tossing once midway through. 

Heat up a Dutch oven over medium-high heat. Add cooking oil and then garlic and onions to heated oil with a dash of salt. Saute until softened, ~3 minutes. 

Next add in butternut squash. Pour in maple syrup and vegetable broth, and then bring to a boil. Simmer for ~10 minutes with lid on. 

After soup has simmered and squash is tender, puree with an immersion / stick blender (like in this video) when it’s cool enough to work with (or transfer into a blender in batches). If using an immersion blender, I like to move the pot into the kitchen sink in case of spattering. Puree until smooth. Season soup to taste with salt and pepper. We use unsalted homemade broth, so we added ~1 1/2 tsp. (7 ml) salt to our final product to make it taste like we wanted. 

Slice pear and toss with kale, toasted bread, raisins, almonds and second part of the vinaigrette. 

Enjoy your soup and salad combination (you can even use some of the toasted bread in your soup too).