In a large bowl add the water, yeast and teaspoon sugar. Allow to sit 5 minutes so it gets foamy.
Add 1/2 cup sugar, eggs, 1/2 cup butter and milk and stir to combine.
Add salt and 4 cups of the flour. Stir to make a sticky dough. Sprinkle 1/2 cup of the remaining flour on your surface and turn out your dough. Add the remaining flour on top and knead, working in the flour until the dough is smooth and elastic--about 5 minutes.
Transfer the dough to a greased bowl. Cover and rise 1 hour or until doubled in size. (This can take up to two hours.)
Transfer the dough to a floured surface and roll to a rectangle--about 18x16 or so. Spread with the remaining 1/2 cup of butter. In a small bowl mix the remaining 1/2 cup sugar, the brown sugar and the cinnamon. Sprinkle this evenly over the dough.
Roll up, starting with the long end and pinch the seam shut with your fingers. Turn the roll seam side down.
Using a sharp knife, starting about 2 inches from one end, cut through the center of the roll all the way down the length. Twist the two cut pieces over each other al the way to the end.
Grease a 12" cast iron skillet. Gently lift the dough into the pan, forming a circle and tuck the end into the center.
Let rise 1 hour or until doubled and then bake at 350 degrees for 35-45 minutes until set in the center. Cover with foil halfway through to prevent over browning.
While the bread bakes, make the frosting. Mix the cream cheese, powdered sugar, milk and vanilla in a small bowl. Spread on while the roll is warm.
To serve, cut slices like you would a pie.