Preheat the oven to 425 degrees Fahrenheit and adjust the rack to the top position. If cooking for four, use both top and middle positions. Wash and dry all produce.
In a medium, dry pan over medium heat, cook the bacon, turning occasionally until crispy, about 6-10 minutes. Transfer to a paper-towel-lined plate to cool and wipe out the pan.
While the bacon cooks, peel and halve the carrots lengthwise, then cut into ¼-inch thick half-moons. Cut the onion in half; thinly slice one half and cut the other half into ½-inch wedges. Slice the peach into ¼-inch thick slices after removing the pit. Halve the buns.
On one side of a baking sheet, toss carrots with a drizzle of oil, salt, and pepper. On the other side, toss onion wedges with oil, salt, and pepper. Roast for 12-15 minutes until the carrots are tender and slightly browned.
Meanwhile, in the bacon pan, melt 1 tablespoon of butter over medium-high heat. Add the peach slices and cook, stirring occasionally until softened, about 6-8 minutes. Reduce heat to medium and stir in peach jam, 2 tablespoons water, ½ teaspoon sugar, and ¼ teaspoon salt. Cook until thickened and most liquid evaporates, about 2-3 minutes.
In a microwave-safe bowl, mix sliced onion with half the balsamic vinegar, 2 tablespoons water, ½ teaspoon sugar, and ¼ teaspoon salt. Cover and microwave for 30-45 seconds. Set the pickled onion aside in a large bowl and reserve the liquid.
Form the ground beef into two patties (or four for 4 servings), slightly wider than the buns. Season with salt and pepper.
Heat a drizzle of oil in a large pan over medium-high heat. Cook the patties until browned, about 3-5 minutes per side. In the last minute or two, top each patty with gouda cheese and cover until melted.
While the patties cook, mix mustard, 2 tablespoons olive oil, salt, and pepper into the reserved pickling liquid. In a separate bowl, combine BBQ sauce and the remaining balsamic vinegar.
Toast the buns, cut sides down, on the oven rack or a baking sheet for 5-7 minutes until golden brown.
Add arugula, sliced almonds, roasted carrots, and the dressing to the bowl with the pickled onion. Toss to combine.
Spread half of the BBQ sauce on the cut sides of the bottom buns. Top with the patties, bacon, caramelized peach, and as much pickled onion as desired. Drizzle with additional BBQ sauce if preferred. Serve the burgers with the salad on the side.