Bring a large pot of water to a boil. Preheat oven to 200°F.
To prepare Sugar Syrup: In a small saucepan combine 1/2 cup sugar and 1/2 cup water; bring to a boil; set aside.
To prepare Tomato Skins: Arrange a rack on a tray. Coat rack with non-stick cooking spray. Score skin on each tomato in 4 equidistant places. Drop several at a time into boiling water until skins loosen, about 10 seconds; set aside to cool. When cool enough to handle, peel off skins; dip 20 pieces of skin into sugar syrup; place on prepared tray. Reserve remaining syrup. Dry tomato skins in oven until crisp but not browned, 30 to 40 minutes; set aside.
To prepare Tomato Jam: Quarter, seed and coarsely chop enough tomatoes to make 2 qt., reserving seeds and juice. Place chopped tomatoes in a heavy saucepan. Add 3/4 cup sugar, the port, ginger, cinnamon and 1/4 tsp. salt. Cook over medium heat, stirring occasionally, until mixture is thick and jam like, about 45 minutes. Remove from heat; set aside until cool; crumble into 1/2" pieces.
Meanwhile, coarsely chop remaining uncooked tomatoes. Place in a blender container with reserved uncooked tomato seeds and liquid. Blend until smooth; strain puree; set aside.
To prepare Tomato Ice Cream: In a medium-sized, heavy saucepan whisk together cream, 1 cup sugar, milk and 1/8 tsp. salt. Heat, stirring frequently, just until mixture comes to a simmer. Meanwhile, in a small bowl whisk egg yolks. Very gradually whisk hot mixture into yolks; return mixture to saucepan. Cook, stirring constantly, just until it simmers. Remove from heat; whisk in 2 cups of the reserved tomato puree and the crème fraiche. Reserve remaining puree, if any, for another sue. Refrigerate, covered, until cool. Transfer to an ice cream maker; process until frozen. Serve or transfer to a freezer container and freeze until ready to serve.
To prepare Basil Syrup: In a heavy saucepan, combine reserved sugar syrup and basil; bring to a boil. Transfer to a blender container; whirl until smooth. Strain and set aside.
To serve: Spread 12 crepes with warm Tomato Jam; roll up. Place 2 crepes on the center of each plate. Top with a scoop of Tomato Ice Cream and a drizzle of Basil Syrup. Garnish with Crisp Tomato Skins.