In a small dish, whisk together the warm water, ½ teaspoon of white sugar, and active dry yeast until the yeast is dissolved. Let it sit for 10 minutes or until the yeast is frothy and bubbly.

In a large bowl, whisk together the warm milk, additional white sugar, melted butter, egg, vanilla, and salt until combined. Whisk in the frothy yeast mixture once it is done proofing.

Gradually add about 2 ½ cups of all-purpose flour while stirring until the dough begins to come together. Then, turn the dough out onto the countertop and knead, adding the last ¼ cup of flour as needed until the dough is just slightly tacky but no longer sticking to your hands. Knead for about 5 minutes total or until the dough is smooth and a finger imprinted in it bounces back. Place the dough back in the bowl, cover, and let rise for 1 hour or until doubled in size.

Punch the risen dough down and transfer to a lightly floured countertop. Roll out into a square or rectangle about ¼ inch thick. Brush the melted butter all over the dough. Combine the brown sugar and cinnamon and sprinkle evenly over the melted butter, followed by the chocolate chips/chopped chocolate.

Cut the dough into squares about 3"x3" using a pizza cutter or knife. Stack the squares of dough before arranging them horizontally in a 9x5-inch loaf pan that has been greased with butter. Sprinkle any of the toppings that fell out over the top of the dough. Cover and let rise for 30 minutes in a warm place while you preheat the oven to 350℉.

Bake the risen loaf uncovered on the middle rack of the preheated oven for 40-45 minutes or until deep golden brown and cooked through. Let cool for 15 minutes before transferring the loaf to a plate to serve or a wire rack to continue cooling.