Place potatoes in a large pot, cover with cold water and bring to a simmer. Simmer gently for 30 minutes or until potatoes are cooked. Place the squash chunks in a large mixing bowl and toss with 1/4 cup of the olive oil, maple syrup, and salt and pepper to taste. Place on a baking sheet and roast in a pre-heated 375˚ oven for 15-20 minutes or until soft. Then strain the potatoes in a large colander in the sink. Transfer back to pot, add the cooked squash and mash with a large fork or potato masher. Season with sea salt and pepper. Next, drizzle half the olive oil on to the potato and squash mix and fold in. Repeat with the rest of the oil and mix well. Taste and adjust seasoning with salt and pepper.