In a medium bowl, whisk the vinegar, sugar, honey, lemon juice, and ¼ cup plus 1 tablespoon ice-cold water until just combined. Set aside.
In a small bowl, beat 1 egg. In a large bowl, sift the flour, cornstarch, and allspice. Add the salt and shortening, then place the bowl of flour over a second bowl filled with ice. Using a plastic bench scraper or a pastry blender, cut the shortening into the flour mixture until it breaks down into tiny pea-size pieces. Create a well in the middle of the mixture, and pour the beaten egg into it. Use a fork to stir the egg, gradually incorporating the flour mixture into it. Gradually add the liquid mixture while continuing to stir with the fork, until a firm, cohesive dough forms. Wrap tightly with plastic wrap, and refrigerate for at least 1 hour or up to overnight.
Line a large baking sheet with several layers of paper towels, and place it near the stove. In a medium pot, add enough oil to reach 2½ inches up the sides of the pot. Heat until the oil registers 340°F on a deep-fry thermometer.
Meanwhile, roll out the cannoli dough: Lightly flour the rollers of a pasta machine. Press the dough into a thin strip, then, starting at the machine’s thickest setting, feed the dough through the rollers and repeat, switching the setting to the next-thinnest each time you roll, and dusting the dough or the rollers lightly with flour throughout the process as needed to prevent sticking. Stop when you’ve reached the thinnest setting.
Transfer the long piece of dough to a clean work surface. Lightly beat the remaining egg. Using a 3½-inch ring cutter, cut out circles from the dough, discarding any scraps. Working in batches of 2 or 3 at a time, wrap the dough pieces loosely around 7⁄8-inch-diameter metal cannoli forms, sealing the overlap with a small amount of the beaten egg.
When the oil is ready, add the prepared 2 or 3 cannoli shells to the oil and fry, turning as needed to cook evenly, until golden brown, about 1 minute total per batch. Using tongs, remove the shells to the baking sheet. Continue rolling and frying the shells. Let cool fully before gently sliding the shells off the molds.
Make the filling: In the bowl of a stand mixer fitted with the whisk attachment, whip the ricotta until smooth, about 30 seconds. Add the robiola or cream cheese, and whip again to combine. Add the powdered sugar, salt, and cinnamon, and continue beating until smooth and combined. Remove the bowl from the mixer, and fold in the chocolate chips. Transfer the mixture to a piping bag fitted with a ½-inch round or starred piping tip. (You can mix cannoli filling up to 1 day ahead and refrigerate.)
Fill the cannoli just before serving: Carefully pipe the ricotta mixture into each end. Gently dunk the ends into more chocolate chips to garnish. Dust lightly with powdered sugar and a pinch of cinnamon if desired, and serve immediately.