Activate the yeast by whisking together warm milk and active dry yeast in a small bowl; let sit for 5-10 minutes until foamy.
In a large mixing bowl, combine light brown sugar, melted unsalted butter, eggs, mashed overripe bananas, and vanilla extract. Mix until smooth and creamy.
Gradually add in 4 cups of bread flour and fine sea salt to the banana mixture; stir well until combined and add about ¾ cup more flour until the dough pulls away from the sides but is slightly sticky.
Knead the dough on a floured surface for about 8-10 minutes until elastic and slightly smooth, or use a stand mixer on medium speed.
Shape into a ball, place in a greased bowl, cover, and let rise in a warm area for 60-90 minutes until doubled in size.
Once risen, punch down the dough, transfer to a floured surface, and roll into a 12x18 inch rectangle.
Spread softened butter evenly across the dough, sprinkle with cinnamon and sugar, and place sliced bananas on top.
Cut into 12 even strips, roll tightly into swirls, and place in a greased 9x13 dish, seam side down.
Cover and let rise again for 30 minutes.
Preheat the oven to 350°F (175°C) and bake for 20-25 minutes until golden brown.
While baking, prepare the frosting by beating cream cheese and softened butter, then mixing in vanilla and maple syrup, and finally adding powdered sugar.
Cool rolls slightly, spread frosting on top, and serve warm.