Preheat your oven to 375 degrees Fahrenheit. Toss the butternut and delicata squash with 1.5 tablespoons of avocado oil and a sprinkle of salt and pepper. Lay the squash pieces on a parchment covered sheet pan in a single layer. Roast for 20 minutes, flip the squash over and roast for an additional 20 minutes, or until the squash is nicely roasted.
Toss the brussels sprouts and cauliflower florets in 1.5 tablespoons of oil, rosemary, garlic, and a pinch of salt and pepper. Lay the brussels sprouts cut side down on a parchment covered sheet pan. Roast for 20 minutes, or until the underside of the Brussels sprouts are golden, then flip over and roast for an additional 10 minutes or until tender.
Massage the chopped kale in the last tablespoon of oil and a pinch of salt and arrange on a sheet pan. Roast for around 10-15 minutes.
Lay the cauliflower on another sheet pan and roast for 20 minutes. Give the florets a shake or flip and continue roasting until browned and tender.
Place a seasoned cast iron pan in the oven to preheat for 15-20 minutes. In a small bowl, combine the avocado oil, red wine vinegar, salt and pepper. Toss the steak in the mixture and allow it to marinate for about 10 minutes.
Once the pan is very hot, place it over a burner on medium heat. Add the steak and sear it for 1-2 minutes on each side. Transfer the pan to the oven and continue cooking until it reaches your desired internal temperature (125 degrees for rare, 135 degrees for medium-rare, 145 degrees for medium). Remove the steak from the pan and allow it to rest for 10 minutes before slicing.
To make the dressing, whisk all of the dressing ingredients together and add salt and pepper to taste.
Combine all of the roasted vegetables together in a large bowl. Top with the sliced steak and apple slices and drizzle on the dressing.