Line a baking sheet with a larger sheet of parchment paper so that the paper extends over the edges of the pan by a couple of inches. Lay the bacon slices on the paper and bake until golden brown and crisp, 20 to 25 minutes. Drain on paper towels until cool.
While the bacon cooks, in a small bowl, stir together the tomatoes, balsamic, salt and sugar. Set aside to marinate at least 15 minutes.
Cut each bacon slice into 4 pieces. Cut the iceberg wedges in half crosswise. On a skewer, pierce a tight section of iceberg, then a tomato half, then a piece of bacon. Repeat with more lettuce, tomato and bacon. Repeat with the remaining ingredients, making 8 skewers.
Serve with a small bowl of Buttermilk Blue Cheese Dressing for dipping, and garnish with cracked black pepper and chives.
Buttermilk Blue Cheese Dressing:
Yield:About 1 1/2 cups
In a small bowl, stir together the mayonnaise, buttermilk, dill, Dijon and pepper until well combined. Gently stir in the blue cheese. Taste and adjust the seasoning with salt and pepper, if necessary. Store in an airtight container in the refrigerator for up to 5 days.