Preheat the oven to 400° convection bake and prepare all ingredients (chop squash and bread, wait until the last minute to slice apples).
On a large sheet pan, lay out 5 strips of bacon to one side of the pan and spread the cubed squash on the other side. Drizzle the squash with 1 Tablespoon each of olive oil and maple syrup and ½ teaspoon of salt. Toss well with your hands and spread out. If your pan is too small for the squash and bacon, you can do on separate pans.
On a second sheet pan, add cubed bread to one side and pistachios to the other, drizzle both with a bit of olive oil and a pinch of salt. Toss well with your hands and spread out. Note** If you buy roasted salted pistachios, you don't need to toast them at all, or you can warm them on the pan for just a few minutes.
*The timing can vary by oven, so keep an eye on things and take them out as they are done, set a timer! Roast both sheet pans together in the oven at 400°. After 10 to 12 minutes, remove the croutons and pistachios and allow to cool, and flip the bacon with tongs. Continue to cook the bacon and squash 10 to 14 more minutes until bacon is crispy and fully cooked. Remove bacon to a plate lined with paper towel to drain and chop. Continue to cook the squash 15 minutes more until cooked through and softened (taste one!). Allow to cool slightly. Remove the squash with a slotted spatula to drain any remaining bacon fat.
Add all ingredients for the dressing to a jar with a lid and shake well (or whisk together in a small bowl).
Assemble the salad. On a large platter, arrange some of the squash as a bed for the greens - especially around the edges so you can see the color. Top it with greens, more squash, croutons, red onion, sliced apples, toasted pistachios, dried cranberries, chopped bacon, Parmesan cheese and drizzle with the dressing (I used all of it but use as much as you like).
Serve the salad, part warm, part cold immediately and enjoy! Or store in the fridge and add the apples, croutons and dressing just before serving.