Preheat oven to 400 degrees F.
Bring a pot of salted water to a boil. Cook the cauliflower for 5 minutes. Strain and saute in a sautepan with a few tablespoons of olive oil until beginning to brown about 5 to 10 minutes. Finish cooking in the oven until nicely browned, about 15 to 20 minutes.
Bring a large saucepot of the cream to a simmer on medium-high heat. Add the elbow pasta to the cream and reduce heat to a simmer. Stir occasionally until almost cooked through, about 10 minutes.
Meanwhile, grind the bacon through a meat grinder (alternatively you can dice the bacon). Grate the Cheddar, truffled sheep's milk, and carmody cheeses. Prepare the cracker crumbs by placing crackers between 2 clean dishtowels and rolling over them with a rolling pin.
When the pasta is just about cooked through, strain, and add the 4 cheeses. Season, to taste, with salt and pepper. Add water to the pasta and cheese, if necessary, to thin it out.
Prepare your casserole dish or individual dishes by placing the roasted cauliflower at the bottom. Top the cauliflower lined casserole dish(es) with macaroni and cheese. Top with cheese cracker crumbs. Return to the oven to bake until hot throughout, about 10 minutes.
Cook the bacon in a small saute pan on medium heat until rendered and crispy, about 10 minutes. Remove casserole from oven and sprinkle with chives and bacon.
*Pure olive oil is a blend of refined olive oil and virgin olive oil. It has a more neutral taste than virgin or extra-virgin olive oil.