Heat the milk up in 30 second increments in the microwave until it is lukewarm. In the bowl of a mixer, combine the milk and yeast. Let sit for 10 minutes. With the dough hook attached, add in the sugar, butter, and eggs. Mix for 1 minute on low speed. Add in 6 1/2 cups of flour and mix for 5 minutes. Cover and let rise for 1 hour.
While the bread is rising, make the caramel sauce by combining the butter, whipping cream, brown sugar, and vanilla in a medium sized saucepan over medium heat. Bring to a simmer, stirring frequently, for 3-4 minutes. Sauce should be completely smooth, and sugar dissolved. Add a dash of cinnamon, and stir to combine.
Add remaining 3/4 cups of flour and mix for 2 minutes. Dough should be smooth, and not too sticky. You will need to lightly grease your hands to handle the dough, but that should be enough to work with it easily. If the dough is still too sticky, add in another 1/4 cup of flour and mix another minute.
Preheat oven to 350. Lightly grease hands with butter and form dough into small balls about 1 inch in diameter. Roll in cinnamon sugar, and place into a bundt or tube pan that's been sprayed with baking spray or greased well. Repeat until all dough is rolled. Depending on the size of your bundt or tube pan, you may have enough dough to do an extra cake pan, or loaf pan. You can also roll the excess dough into cinnamon roll form if you are feeling frisky, or fry them into donuts while you wait for your monkey bread to rise.
Let the monkey bread rise for 30-40 minutes in a warm, draft-free place. Gently pour 1/2 of the caramel (or as much as will fit leaving 1 inch space at the top of the pan) over the bread, and then bake at 350 for 30-45 minutes, or until the dough is golden brown and cooked all the way through.
After you pull the bread out of the oven, invert the pan onto a baking sheet and let cool for 5 minutes before removing. You may have to pry out the bread a bit. Pour the caramel sauce over the monkey bread, and serve warm!