Preheat the oven to 400˚F. Line one large baking sheet and one small baking sheet with parchment paper.
Spread the diced butternut squash on the large baking sheet and add the garlic cloves, 1 ½ teaspoons of the sage, the balsamic vinegar and 1 tablespoon of the olive oil. Season with salt and pepper. Mix everything around on the pan to coat. Roast, stirring occasionally, until the squash is tender and caramelized around the edges, about 30 minutes. Taste and season with additional salt and pepper, if needed. Let cool (reserve the roasted garlic cloves for the dressing). Do Ahead: The squash can sit at room temperature for several hours or it can be refrigerated overnight.
While the squash bakes, make the maple pecans. Pour the pecans onto the small baking sheet and drizzle with 1 tablespoon of the maple syrup. Season with salt. Toss the pecans to evenly coat in the syrup, then spread them in an even layer. Slide the pan in the oven (this can be alongside the squash) for about 5 minutes, or until the nuts are a shade darker in color and aromatic. Cool completely (the nuts will harden as they cool). Coarsely chop. Do Ahead: The maple pecans can be refrigerated for up to 1 week.
Squeeze the roasted cloves out of their skins into a small bowl, and mash them to a paste with a pinch of salt. Add the apple cider vinegar, the remaining ½ tablespoon maple syrup and the remaining ½ teaspoon sage. Season with salt and pepper. Whisk in the remaining ¼ cup extra virgin olive oil. Do Ahead: The dressing can be refrigerated for up to 1 week.