Before starting, preheat the oven to 425°F and wash and dry all produce.Heat Guide for Step 1: 1/8 tsp mild, 1/4 tsp medium, 1/2 tsp spicy and 1 tsp extra-spicy! Finely chop 2 tsp sage leaves (dbl for 4 ppl). Toss squash, half the sage, 1/2 tbsp oil (dbl for 4 ppl) and 1/4 tsp chili flakes (NOTE: Reference Heat Guide) on a baking sheet. Season with salt and pepper. Roast in middle of oven, stirring halfway through cooking, until golden-brown and tender, 20-22 min.

While squash roasts, heat a large non-stick pan over medium heat. When hot, add pepitas to the dry pan. Toast, stirring often, until golden-brown, 4-5 min. (TIP: Keep your eye on them so they don't burn!) Transfer to a plate and set aside.

Add 1/2 tbsp oil (dbl for 4 ppl), to the same pan, then onions. Cook, stirring occasionally, until slightly softened, 3-4 min. Add 1 tsp sugar (dbl for 4 ppl) and season with salt. Cook, stirring occasionally, until dark golden-brown, 3-4 min. Remove the pan from heat, and stir in half the vinegar. Set aside.

While onions caramelize, stir together stracciatella and remaining sage in a small bowl. Season with salt and pepper. Arrange naan on another baking sheet. (NOTE: It's ok if they overlap! Bake naans in 2 batches, for 4 ppl.) Divide stracciatella mixture between naans. Toast in in the top of the oven, until golden-brown, 6-7 min.

Top toasted naan with roasted squash and caramelized onions. Sprinkle over toasted pepitas. Toss arugula with remaining vinegar and 1 tbsp oil (dbl for 4 ppl) in a medium bowl. Season with salt and pepper.

Cut flatbread into pieces, then divide a few pieces and arugula salad between plates.