This deeply flavorful glaze can be made up to 1 day ahead of time.
Combine first 5 ingredients in a saucepan over medium heat. Cook 16 minutes or until mixture thickens slightly. Remove from heat; stir in vanilla and 2 teaspoons black pepper.
Combine olive oil and next 4 ingredients in a bowl. Place pork on a jelly-roll pan; rub with marinade. Refrigerate 6 hours or overnight. Remove pork from refrigerator, and let stand at room temperature 1 hour before cooking. Brush off marinade; sprinkle with 2 tablespoons salt and 1 tablespoon pepper.
Preheat oven to 350°. Heat 6 tablespoons canola oil in a large heavy-bottomed roasting pan over medium heat. Place pork, fat side down, in pan; cook 18 minutes, turning to brown all sides. Transfer pork to a plate, and wrap exposed bones with aluminum foil. Pour off fat from pan.
Add remaining 2 tablespoons canola oil to roasting pan. Add radicchio and fennel, cut sides down, to pan; cook 8 minutes, turning to brown all cut sides. Remove from pan. Return pork to pan, fat side up.
Roast pork 1 hour or until interior registers 115° when tested with a thermometer. Remove pan from oven. Arrange fruit and vegetables around roast; sprinkle vegetables with remaining 1 teaspoon salt. Brush top of roast with half of cranberry mixture, and return pan to oven; roast 20 more minutes or until interior registers 140° when tested with a thermometer. Remove pan from oven.
Transfer roast to a large plate; remove foil from bones. Let rest 10 minutes. Arrange vegetables and fruit on a large platter; place roast on platter. Pour any accumulated juices from plate into remaining cranberry mixture. Brush pork with 1/2 cup cranberry mixture. Serve pork roast, vegetables, and fruit with remaining cranberry mixture. Garnish, if desired.