Preheat the oven to 400˚F, and line a baking sheet with parchment paper. (I use my toaster oven for a quicker preheat.)
Slice off the ends of the delicata squash. Stand one of them on end, hold onto it firmly, and slice it in half lengthwise. Use a spoon to scoop out the seeds and pulp.
Slice into ½" slices, and repeat with the other delicata squash.
Toss with 2 tablespoons olive oil, and sprinkle with ½ teaspoon salt, the paprika and chipotle pepper powder. Roast for 15 minutes.
De-stem the kale leaves by either cutting them away from the tough center stem using a sharp knife, or hold onto the stem's bottom, and sweep your other hand up the stem to tear away the leaves.
Wash and thoroughly dry the kale leaves. Place them in a bowl, drizzle with the remaining 2 tablespoons olive oil and remaining ¼ teaspoon salt. Lightly massage the leaves until they begin to limp. If you measure them out, they've collapsed into about 5 cups.
Toss with the vinegar, roasted squash, avocado and pumpkin seeds.