Place raisins in a small saucepan; cover with water. Heat to boiling; remove from heat and let stand 5 minutes. Drain and discard water.
Combine raisins, pineapple and preserves in small food processor; pulse until almost smooth.
Butter the bottom and sides of a 6-cup ovensafe mold. Line bottom with baking parchment or waxed paper. Place a layer of ladyfingers in bottom, covering bottom fully. Spread 3 tbsp of fruit mixture over ladyfingers. Stand ladyfingers, touching side by side, around sides of mold, lining it completely.
Beat eggs in a medium bowl. Add 1/2 c sugar, milk and Cointreau.
Ladle 1 c of custard mixture into mold. Top with another layer of ladyfingers. Spread another 3 tbsp fruit over ladyfingers. Pour in 1/2 c custard mixture. Continue layering ladyfingers, fruit and custard until all are used up.
Cover mold tightly with aluminum foil. Place mold in large roasting pan. Place pan on oven rack and pour boiling water around mold to 1 below the top of the mold. Bake in preheated oven 2 hours or until top is firm. Transfer mold to a rack and cool 1 hour. Place mold in refrigerator and chill at least 4 hours or overnight.
To unmold, run a thin knife around the inside of the mold. Place a plate over the top of the mold and invert; remove mold.
Chill beaters and bowl thoroughly. Beat whipping cream with 2 tbsp sugar and vanilla extract until stiff. Spoon whipped cream into piping bag with star tip. Pipe ribbons of cream around sides of mold; pipe circles of rosettes around the top of the mold. Garnish with candied pineapple or glacéed cherries.