When using fresh butternut squash, I usually put the squash in the microwave and cook it on high for 8 min. or more. It softens it enough to be able to peel it and cut it without inflicting bodily injury.
Heres a quick alternative I concocted on a test basis this weekend, using Green Giant frozen cooked winter squash (no additives, nothing but the squash flesh cooked & pureed to a smooth consistency). It got the family stamp of approval and I will serve it on T-day:
Toast the garlic, if used, in a few drops of olive oil. Add the chopped onion, saute in part of the stock. Add remainder of stock and rest of ingredients. Cook, uncovered, over medium heat until apples have cooked down and soup has reduced to a light creamy consistency (about 25 min).