Thinly slice shallot. Cut apple into thin matchsticks. In a medium mixing bowl, stir together shallot, apple, lemon juice, sugar and ¼ teaspoon salt; transfer to a fine–mesh strainer. Set strainer in mixing bowl; set aside at least 15 minutes.
In a skillet set over medium heat, stirring constantly, toast fennel seeds and caraway seeds until fragrant, 2-3 minutes. Transfer seeds to a large mixing bowl; set aside. Remove discolored or woody stems from brussels sprouts; cut in half through stems. Using a food processor with slicer attachment, or by hand with a knife, thinly slice all brussels sprouts. Transfer brussels sprouts, rosemary, raisins and pumpkin seeds to bowl with spices and toss to combine; set aside.
Whisk together olive oil, apple cider vinegar, brown sugar, mustard, maple syrup, cinnamon, nutmeg, pinch cayenne, ½ teaspoon salt, and black pepper to taste, until evenly combined. Stir apple mixture and press gently to remove excess moisture; add apple mixture to shredded brussels sprouts. Pour vinaigrette over brussels sprouts; toss thoroughly to combine. Cover and rest 30 minutes, or refrigerate overnight. Toss to redistribute vinaigrette and serve.