Preheat oven to 425 degrees Fahrenheit and line a baking sheet with parchment paper or foil.
Rinse sweet potatoes and pat dry. Lightly coat potato with olive oil, arranging them side by side unto one end of the prepared baking sheet. On the other end, add the sliced apples, drizzle with olive oil, and sprinkle on cinnamon and nutmeg. Bake for 25-30 minutes or until tender and juices begin to bubble outside of skin of the sweet potatoes and the apples have wilted and become golden. Remove from oven, let cool for 10-15 minutes and slice in half. Remove sweet potato 'flesh' (insides) and place in a bowl.
In a bowl, add the pecans, oats, honey, flour, cinnamon, and butter together, mixing until combined and moist.
Spread the topping mixture (grouped into clusters) onto a baking sheet lined with parchment paper and bake for 15-20 minutes, until everything has turned golden, and baked "together" in clusters. NOTE: Please avoid stirring or tossing! In order to create clusters/chunks, you should bake it without touching!!
In a medium-sized dutch oven pot over medium-high heat, add the olive oil. Once heated, add the minced garlic and onion and sauté until fragrant, about 1-2 minutes. Remove from heat and add the sautéed garlic in a high-powered blender along with the roasted apples, flesh of the sweet potato, and vegetable stock. Blend on high-speed until everything is fully broken down and smooth.
In the same medium-sized dutch oven pot over medium-high heat, add the blended sweet potato-apple mixture along with the heavy cream, honey, salt, black pepper, smoked paprika, oregano, basil, parsley, garlic powder, and cayenne pepper, stirring everything together until combined.
Add in the shredded or grated cheddar cheese and stir until combined and melted.
Let everything boil for 1-2 minutes and then reduce heat to low to allow a simmer for another 5-6 minutes.
At this point, the soup should be thickened as it continues to simmer.
Remove from heat and serve immediately into prepared bowl(s), top with cinnamon pecan topping, and a side of bread, if desired.
Bon Appetit!