Place ham in extra-large pot and cover with water. Bring to a boil over medium heat; reduce heat and simmer for 1 ½ hours.
Preheat oven to 350°F. Drain ham, then pat dry. Transfer to a roasting pan, fat-side up.
Using a paring knife, cut vanilla in half lengthwise and scrape the seeds. In bowl, whisk together vanilla seeds, maple syrup, orange juice, and pepper.
Using a knife, cut diamond-shaped notches about 1/4-inch deep into surface of the fat.
Insert vanilla pieces into diamonds, then brush with some of the maple mixture. Roast for 1 1/2 hours, basting often with the cooking liquid.
A few minutes before removing from the oven, sprinkle ham with maple sugar and roast until caramelized.
To serve, transfer ham to a platter. Strain the juices from the roasting pan and serve with ham.
Notes
Tip: Save the scraped vanilla pod and cut it into 12 to 15 pieces to stud the ham.