For dressing: Whisk vinegar and lemon juice in small bowl; gradually whisk in oil. Season with salt and pepper.
For salad: Preheat oven to 400°F. Brush 2 large rimmed baking sheets with oil; spray with nonstick spray. Whisk vinegar and sugar in small bowl; set aside. Cut squash halves crosswise into 1/4-inch-thick slices. Arrange squash in single layer on prepared sheets; brush with oil and sprinkle with coarse salt and pepper. Roast 5 minutes; brush with sugar-vinegar mixture. Turn squash over and brush with sugar-vinegar mixture; roast 5 minutes. Roast until squash is tender when pierced with small knife, about 15 minutes longer. Cool on sheets. DO AHEAD: Can be made 4 hours ahead. Let stand at room temperature. Arrange 5 to 6 endive leaves on each of 10 plates. Place butternut squash slices in center of each plate. Scatter apples, cheese, and cranberries over squash. Drizzle dressing over and serve.