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Place dates in a heatproof bowl and cover with boiling water; let soak 10 minutes. Drain and transfer dates to a blender or food processor. Add coconut milk, salt and vanilla; blend until smooth. Store in an airtight container and refrigerate for up to 2 weeks.
Add all ingredients to a blender. Blend on high just until smooth, about 20 seconds. Transfer to a covered container and refrigerate overnight.
Whisk together coconut milk, coconut cream (or yogurt) and 2 tablespoons date caramel. Stir in chia seeds until evenly combined. Transfer to a covered container and refrigerate overnight.
Add about ⅓ cup overnight oat pudding to the bottom of each of four 8-oz jars. Spoon about ¼ cup chia pudding over the oat layer. Top with another ⅓ cup oat pudding to fill the jars, making sure to leave enough space to add the toppings and place the lids on the jars. Finish with a thin layer of remaining date caramel and top with chopped dates and flaky salt.