Preheat the oven to 350 degrees. Place the asparagus on a baking sheet in 4 bunches of 4 or 5. Place 2 pieces of bacon over each bunch, forming an X. Bake for about 15 minutes, or until the asparagus is partially cooked. Remove from the oven, leaving the oven on.
Lightly toast the bread in the oven. In a small bowl, combine the oil and garlic and brush on the bread. Transfer each bundle of asparagus and bacon to a slice of bread and top with a slice of cheese. Place on the baking sheet and bake for an additional 3 to 5 minutes, or until the cheese is melted.
To serve, spoon 1/4 of the vinaigrette on each of 4 plates. Place a warm toast on each pool vinaigrette.
To make the vinaigrette: In a medium bowl, whisk together the oil, vinegar, salt, and pepper. Stir in the chives, olives, shallots, and bell pepper; set aside.