Pour milk at 110–115°F into a stand mixer bowl. Add yeast and let stand a couple of minutes. Mix in softened butter, sugar, and eggs. Add salt and 4 cups flour and mix with beater blade just until combined. Rest 5 minutes.

Switch to a dough hook and knead on medium 5–7 minutes, until smooth, elastic, and slightly sticky. Add reserved flour 1 tablespoon at a time only if too wet to handle. Transfer to a greased bowl, cover, and rise in a warm place for 30 minutes.

Mix softened butter, brown sugar, cinnamon, vanilla extract, and butter extract into a spreadable filling.

Beat cream cheese and butter for the frosting until combined. Add maple extract and powdered sugar and beat on high for 3–5 minutes. Set aside.

Roll dough on a floured surface into a large rectangle about ½ inch thick. Spread filling over it, trim edges, roll tightly from the long side, and cut into 8–12 slices about 2 inches thick. Place in a greased 9×13-inch pan. Cover and rise 20 minutes or until nearly doubled.

Preheat oven to 375°F. Warm heavy cream slightly and pour evenly over rolls immediately before baking.

Bake 20–22 minutes, until lightly golden and baked through. Cool slightly, then spread maple cream cheese frosting over warm rolls and serve.