Trim the woody ends from the asparagus spears by bending each one gently until it snaps naturally at the tender point—this ensures you'll only have the best, most tender part. Pat the trimmed asparagus dry with paper towels, as this helps the bacon crisp better during baking. In a small bowl, combine the salt, pepper, and garlic powder to create your seasoning blend. Toss the asparagus lightly with about half of this seasoning mixture, coating them evenly.
Preheat your oven to 400°F and line a baking sheet with parchment paper or foil for easy cleanup. Divide the seasoned asparagus into 9 bundles of 3 spears each. Wrap one bacon slice around the middle of each bundle, laying it flat on the baking sheet seam-side down so it stays secure during cooking. I like to wrap the bacon slightly diagonally for a more polished presentation, though any secure wrap works just fine.
Divide the butter into small pieces and dot it evenly over each asparagus bundle, using about 1 teaspoon per bundle. Sprinkle the remaining seasoning blend over the top of each bundle. The butter will melt during baking and help crisp the bacon while keeping the asparagus moist and flavorful.
Place the prepared baking sheet in the preheated 400°F oven and bake for 20-25 minutes, until the bacon is crispy and browned and the asparagus tips are just beginning to caramelize at the edges. The exact time depends on your oven and the thickness of your bacon, so start checking around the 18-minute mark. When done, the bacon should be fully rendered with no soft, chewy spots.
Remove the baking sheet from the oven and let the bundles cool for just 1-2 minutes so they're still warm but handleable. Brush or drizzle the reduced balsamic vinegar over each bundle, coating them lightly. The warm asparagus and bacon will absorb the tangy-sweet glaze beautifully, adding a sophisticated finish to the dish. I find that reduced balsamic works best here because it clings to the bundles rather than running off—if your vinegar isn't already reduced to a syrup, simmer it in a small pan until it thickens before using.