Pour flour, eggs, sugar, salt, yeast, milk, orange zest, and vanilla extract into a bowl of a stand mixer equipped with the dough hook attachment.
Turn on the mixer and knead for 10 minutes at medium speed or until the dough separates from the bowl edges.
Add the softened butter cut into cubes piece by piece waiting until the previous one is incorporated.
Mix and add butter until all the butter is incorporated; scrape down the sides using a rubber spatula.
Mix at medium-high speed for 10-15 minutes or until the dough looks nice and smooth and passes the windowpane test. Add the chocolate chips and mix again for one minute until well combined.
Stop the mixer and move the dough into a greased large bowl. Cover with plastic wrap and let proof in a warm place for 1 hour or until double in size.
Put your fist in the dough, push down on it to deflate it, and place it in the refrigerator overnight.
Next day, place the dough on a lightly floured surface, divide it in half, and form 2 balls. Poke a hole in the center and give it a large oval shape. Repeat the process with the other dough ball.
Transfer the Rosca de Reyes to two baking sheets lined with parchment paper. Cover with wrap or kitchen cloth and let proof in a warm place for a couple of hours or until doubled in size.
While the dough is proofing, make the cookie paste. Beat softened butter, powdered sugar and vanilla extract until well combined, then add sifted flour and mix until well combined. Shape the cookie paste into a rectangle, cover it in plastic, and refrigerate for 15 minutes. After resting, cut the cookie paste into four or six equal strips.
Brush the wreaths with egg wash and decorate the top of the rosca with candied fruits, guava paste, and cookie paste. Bake in a 350°F preheated oven for 20/25 minutes or until the bread reaches an internal temperature of 190°F/87°C.
Remove the bread from the oven and place it on a wire rack to cool down. After the Rosca is cooled, insert the baby figurine from the bottom of the bread so no one can see it where it is.