Combine warm water and sugar in a medium bowl.
Sprinkle yeast over top and set aside until foamy, about 5 minutes.
Add 4 cups flour and salt, stir with a wooden spoon until a shaggy dough forms.
Turn out onto a lightly floured surface and knead until dough comes together, about 10 times.
Lightly oil a medium-size bowl. Add dough and turn to coat. Cover with plastic wrap and set aside until doubled in size, about 90 minutes.
Combine brown sugar, butter, and maple syrup in a 10-inch skillet, preferably cast iron. (If you don't have a 10 inch skillet, you can do this in whatever skillet you have, and then swiftly transfer the toffee mixture to a 10-inch cake pan.)
Cook, stirring often, until sugar dissolves and mixture is evenly bubbling across the surface, 2-3 minutes.
Let cool slightly, then sprinkle with nuts. Set aside.
Preheat oven to 350°F.
Combine butter, dates, brown sugar, and salt in a medium saucepan and place over medium-high. Cook, stirring often, until butter melts.
Continue to cook, stirring and mashing to help break up dates, until mixture comes to a boil and dates are broken down, about 4 minutes. Let cool to room temperature.
Once the dough has doubled in size, turn out onto a lightly floured surface.
Divide dough in half (this will make it easier to work with).
Working with one at a time, roll each piece into a 12- x 16-inch rectangle.
Divide date mixture between the two pieces of dough, spreading all the way to the edges. Sprinkle each piece with 2 teaspoons cinnamon.
Starting from the long end, roll up dough and place seam-side down.
Cut dough crosswise into 2-inch spirals. Transfer rolls, cut sides down, to prepared skillet or cake pan, arranging snugly to fit.
Bake until golden and risen, 30-35 minutes. Let cool 5 minutes before inverting onto a rack. Let cool slightly before eating.