Add 1 cup milk and butter to a medium saucepan and heat until hot but not yet boiling. Remove from heat and allow the mixture to cool until still warm to the touch, but not hot.
Sprinkle the yeast over the top of the butter/milk mixture, stir gently, and allow it to sit for 10 minutes.
In a separate bowl, whisk together flour and salt and set aside.
In the bowl of an electric mixer, beat ⅓ cup sugar and 2 eggs with the paddle attachment until combined. Pour in the butter/milk/yeast mixture and mix to combine.
Add half the flour/salt mixture and beat on medium speed until just combined. Add remaining half and mix again until combined.
Switch to the dough hook attachment on your mixer and knead the dough on medium speed for about 10 minutes. If your dough feels too sticky at this point, add another ¼ C of flour and beat for 5 more minutes.
Pour some canola oil into a large bowl and toss the dough in the oil to coat. Cover the bowl with plastic wrap and find a warm place to set the bowl for 2 hours.
On a lightly floured surface, roll the dough into a large rectangle, about 18-24 inches long. Make sure it’s not wider than the length of the loaf pan you’re going to use.
Mix together remaining ⅓ C sugar and cinnamon and and smear some melted butter on your dough rectangle. Sprinkle the cinnamon/sugar evenly over the dough. Sprinkle raisins on if you're planning to use them.
Starting at the far end, roll the dough toward you, keeping tight and contained. Pinch the seam to seal it and place in a well-buttered loaf pan seam-side down. Cover pan with plastic wrap and allow to rise for another 2 hours.
Pre-heat oven to 350 degrees. Mix remaining egg and 2 Tbsp milk together and smear over the top of the loaf.
Bake bread for 40 minutes on the middle or lower rack of your oven. Allow bread to cool before slicing.