Preparing the dough: Heat milk to be warm to the touch (about 110° F). Using a stand mixer* with a dough hook, combine the warm milk, yeast, and sugar together. Add 3 cups of flour and begin to mix.
Add your first 3 cups of flour and mix together. Once it's mostly incorporated, add softened butter, eggs, and salt. Continue to mix on low.
Slowly add the additional 2 ½ cups of flour. In pouring your last cup, do so slowly, watching the dough. Add additional flour as needed, just a little at a time. When you've added enough flour, the dough will be soft and slightly sticky. It will also be pulling away from the bowl. You don't want a tough dough. Leave the mixer on for an additional 8-10 minutes to knead.
Take your dough hook out, and cover the bowl to let the dough rest and rise for about 30-40 minutes.
Filling: In a medium size pot over the stove, combine all of the filling ingredients and let it get to a simmer. Simmer occasionally and let it simmer for about 8-10 minutes to let it start to thicken. Remove from the heat and store in the refrigerator while you wait to to assemble in your rolls. (This is an easy step to make in advance earlier in the week as well!)
Assembly: When the dough has about doubled, punch it down and place on a clean, floured work surface. Use a rolling pin to roll the dough out into about a 14x18 inch rectangle, making sure the dough is smooth and even in the corners. Spread an even layer of the raspberry filling.
Tightly roll it up into a log. You can roll either direction. I like to roll from the short end to make a nice thick log. Rolling from the long end will create a slightly skinnier, longer log which will yield more rolls. Use a strand of floss to cut into 1 inch sections and place in a greased jelly roll pan or baking pan, leaving about 1-2 inches in between so the rolls have room to grow. Rest & Bake: Overnight Instructions: Cover well with sprayed plastic wrap and let them rest in the fridge overnight. The next morning, preheat the oven to 350°F and let the rolls get back to room temperature and rise (usually takes about 1 hour). Baking immediately: Keep the rolls in a draft free place and let them rise until they've grown and the dough gets soft and puffy, usually about 25 minutes. While they're resting, preheat the oven to 350°F. Bake for 16-20 minutes. I like to cover them with foil about half way through so they don't brown as much on top. They're done when the tops and bottoms are starting to get lightly golden and it doesn't look doughy. Frosting: While the rolls bake, make the frosting (or make in advance night before). Beat the butter and cream cheese together, then add remaining ingredients and beat until light and spreadable. Spread the frosting on while warm and serve immediately.
Storing: Store airtight for up to 5 days. You can freeze them, but I recommend freezing the rolls plain and adding the glaze day of for best results. Heat up slightly before serving for the ultimate gooey treat! Enjoy!