Add the warm water and dried cranberries to a small bowl. Set aside to soak for 10–15 minutes while you prepare the pancake batter, then drain well.
In a medium bowl, combine the butternut squash purée and buttermilk. Blend with an immersion blender until smooth. Add the eggs, vanilla, melted butter, and brown sugar and blend to combine.
In a large bowl, whisk together the flour, baking soda, baking powder, salt, and cinnamon.
Add the wet ingredients to the dry ingredients and fold with a rubber spatula until just combined. Gently fold in the drained cranberries and chocolate chips.
Let the batter rest for 15–30 minutes at room temperature.
Meanwhile, make the toasted pecan maple syrup: Toast the pecans in a small saucepan over medium heat until fragrant and beginning to brown, 3–4 minutes. Add the maple syrup and butter and cook until the bubbling diminishes slightly, stirring throughout to keep from burning, 3–4 minutes. Remove the pot from the heat and keep warm until ready to serve.
Melt 1 tablespoon of butter in a medium skillet over medium-low heat. Once the butter begins to foam, add ⅓ cup (40 G)of pancake batter to the pan. Cook for 2–3 minutes, until bubbles start to appear on the surface. Flip the pancake and cook for another 2–3 minutes on the other side, until golden brown and cooked through. Transfer the pancake to a platter and repeat with the remaining batter, adding more butter as needed. As you cook the pancakes, keep them in the oven at 200°F (95°C) or cover with foil to keep warm.
Serve the pancakes warm with the toasted pecan maple syrup on top.