In a small bowl, mix two tablespoons of milk with the cornstarch until smooth. Set aside.
Whisk the cream cheese in a medium bowl until smooth or almost smooth (some lumps and bumps are just fine).
In a 4 quart saucepan, combine milk, cream, sugar, and corn syrup, then bring to a rolling boil. Boil for 4 mins.
After 4 minutes, remove the milk mixture from heat and gradually mix into your cornstarch slurry mixture that you made in Step 1. Add back to the saucepan, and cook over medium high heat for about 1 minute, or until thickened and it coats the back of a wooden spoon. Remove from heat.
Gradually whisk the milk mixture into the cream cheese. Add both of the extracts, orange juice, zest, and buttermilk. Lastly, I add in the kosher salt, to taste. Please note: the amounts of the extracts were ball parked; I really wanted a robust flavor, so i just kept adding until I was happy with the flavor. Taste as you go – you may want more or less depending on your personal preference.
Fill a large bowl with ice water. (Make sure your medium bowl in the next step will fit with a little room to spare.) Set aside.
Once all ingredients are incorporated, pour base into a medium glass bowl and place in ice bath. Let stand until very cold, half an hour or so. Continue adding more ice as needed. Stirring occasionally will speed up the process.
Once the mixture is cold, pour into ice cream maker, making sure to scrape out all the goodness and freeze according to manufacturer’s instructions.
While ice cream is churning, melt chocolate and butter in a small saucepan over low heat or in the microwave in 15 second bursts. When chocolate is melted and smooth, transfer to a zip-top bag and seal well, pressing out as much air as possible. If necessary, place bag in a bowl of warm water to keep warm while the ice cream finishes churning.
When ice cream is the consistency of soft serve, 1-2 minutes before being completely done, cut 1/4 inch off the corner of the bag. Slowly drizzle most of the chocolate into churning ice cream, allowing the chocolate to swirl throughout.
Transfer to a freezer safe container and store until texture is hardened (3-4 hours, or preferably overnight). Once ready to serve, let the ice cream sit out for 10 or 15 minutes until softened.