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Warm milk in the microwave until it hits 100–110°F (about 60–90 seconds total).
In a large bowl, whisk warm milk and yeast. Let sit for 5–10 minutes until foamy.
Add in brown sugar, melted butter, eggs, mashed bananas, and vanilla. Mix well.
Add 4 cups of flour and salt. Begin mixing, then slowly add up to ¾ cup more flour until the dough pulls away from the sides and is only slightly sticky.
Knead by hand or mixer for 8–10 minutes. Form into a ball, place in a greased bowl, cover with a towel, and let rise in a warm area for 60–90 minutes or until doubled in size.
Roll dough out onto a floured surface into a 12×18 inch rectangle.
Spread softened butter across the surface.
Mix brown sugar and cinnamon. Sprinkle evenly on top of the butter.
Lay banana slices across the surface.
Cut into 12 even strips, then roll each into a swirl. Place into a greased 9×13 dish.
Cover and let rise again for 30 minutes.
Bake at 350°F for 20–25 minutes, until golden brown.
Beat cream cheese and butter together until smooth.
Add in vanilla and maple syrup. Beat again.
Gradually add powdered sugar until desired consistency is reached.
Spread frosting on warm rolls fresh out of the oven. Serve immediately.