Preheat oven to 425°F.
Fill large pot with potatoes and salted water. Bring to a boil over high heat and cook until potatoes are fork tender, about 15 minutes. Meanwhile, steam cauliflower in a pot until fork tender. When potatoes and cauliflower have finished cooking, drain water and set potatoes and cauliflower aside in bowl or colander.
While potatoes and cauliflower are cooking, line rimmed baking sheet with parchment paper. To prepare broccoli, remove bottom part of stem, and slice into bite-sized florets leaving an inch of the stem intact. Place broccoli on prepared baking sheet, lightly drizzle with 1 tablespoon olive oil and sprinkle with pinch of salt and ½ teaspoon garlic. Roast in oven for 20 minutes until crispy. (Cooking tip: Boil or microwave broccoli for the topping if you don’t want to fire up your oven for roasted broccoli.)
Heat 1 tablespoon olive oil over medium heat. Sauté leeks, crushed red pepper, and garlic until leeks soften, about 1-2 minutes. Remove pot from heat, and add potatoes, cauliflower, vegetable stock, milk, and ½ teaspoon salt.
Using an immersion blender, (or transfer soup to regular blender), puree soup until smooth and creamy. Place pot back on stove and heat through.
To serve, ladle one cup of soup into a bowl and top with cheese, bacon, chives, and roasted broccoli.