Season the squash with salt and pepper. Place the squash halves with the cut side down into a glass baking dish. Pour the water into the dish.
3
Bake the squash in the preheated oven for 1 hour. Scrape the squash with a fork into a bowl. Save the dish for later use. Keep the oven hot.
4
Cook the Italian sausage in a large skillet over medium heat until browned on all sides, 5 to 7 minutes. Remove the sausage from the skillet, reserving the oil, and set aside to cool. Add 2 teaspoons olive oil to the skillet and allow to get hot; cook and stir the onions and garlic in the hot oil until the garlic is browned and the onions are translucent, 7 to 10 minutes. Chop the cooked sausage and add to the mixture along with the squash. Season with the oregano, salt, and pepper. Reduce heat to medium-low and simmer for 10 minutes, stirring occasionally. Transfer the mixture to the glass baking dish.
5
Arrange the apple slices over the mixture in the baking dish. Drizzle 1 teaspoon olive oil over the apples. Scatter the almonds over the apples and sprinkle with the Monterey Jack cheese.
6
Bake in the preheated oven until the the cheese is melted completely, about 15 minutes. Serve hot.