In a medium bowl, whisk together the mayo, sour cream, buttermilk, whole milk, white wine vinegar and black pepper until smooth and creamy. Fold in the blue cheese. Cover and refrigerate until you are ready to serve.
Bring a large pot of water to a boil. Add the eggs and cook for 6-7 minutes for a soft-boiled egg. Remove from heat and transfer immediately to an ice bath. Once cool, peel and cut them in half. Set aside.
Preheat your grill or grill pan over medium-high heat. If using a regular grill, place a large cast iron skillet directly on the flame to heat up. Once heated up, add the bacon slices and cook, turning occasionally until crisp. Remove from heat and chop.
Assemble your iceberg wedge salads by layering crispy bacon, toasted bread crumbs, and eggs on top of the wedges. Drizzle with blue cheese dressing and sprinkle with black pepper. Serve immediately.