To make the dough, warm the milk to about 95 F. Pour the warm milk into a stand mixer and stir in the sugar and yeast. Let it sit for about 5 minutes.
Grease a large bowl and set aside.
Add the flour, eggs, vanilla extract, butter, and salt to the yeast mixture and mix until it forms a ball of dough.
Transfer the dough to a lightly flowered surface and knead for a couple seconds.
Place the dough in the greased bowl, cover, and place somewhere warm for 2 hours or until it doubles in size.
To make the Caramel, place the butter, brown sugar, maple syrup, salt, and vanilla extract into a saucepan and cook for 3-4 minutes or until smooth and thick. Set aside.
Place the risen dough onto a lightly floured surface and roll into a 12x18 rectangle using a rolling pin.
To make the filling, combine the brown sugar and cinnamon.
Spread 1/2 cup softened butter all over the dough and sprinkle all of the filling mixture on top.
Tightly roll the dough into an 18-inch log and slice into 12 even rolls using dental floss.
Pour the caramel into a 9x13 greased baking dish and place the 12 rolls on top of the caramel. Cover the rolls and let them rise someplace warm for 45 minutes or until they double in size.
Preheat the oven to 375 degrees F.
Place the rolls in the oven for 25-30 minutes or until done.
Invert the baking dish onto a larger serving platter and serve warm.