Whisk all dressing ingredients together and set aside.
Preheat grill to high heat. Season flank steak evenly with salt and pepper. Grill approximately 3-4 minutes per side for medium rare, flipping once. Set aside, tented loosely with foil and rest on cutting board for at least 10 minutes before slicing.
While steak rests, prepare grilled tomatoes and avocados. Slice each tomato in half horizontally. Place tomato and avocado halves cut sides down directly on hot grill for approximately 30 seconds. Gently remove tomatoes and avocado to a cutting board. Cut each grilled tomato half into four pieces. Scoop out each half of the avocado from skin and chop into bite-sized pieces.
Gently toss arugula and sliced romaine lettuce in a small amount of dressing, coating lightly and evenly. Arrange dressed greens evenly on four serving plates.
Slice rested flank steak thinly across the grain and arrange over the greens. Season steak slices with salt and pepper. Arrange sliced red onion, grilled tomato and grilled avocado pieces on top. Season the vegetables with additional salt and pepper and an extra light drizzle of salad dressing.
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