In a large bowl, beat cream until soft peaks form. In another bowl, beat cheeses until light and fluffy. Beat in cooled chocolate, ½ cup confectioners’ sugar and vanilla. Fold in 2 cups of the whipped cream.
Brush half of the ladyfingers with half of the orange juice, arrange in a 13-by-9-inch dish. Spread with 2 cups cream cheese mixture; top with half of the strawberries. Brush remaining ladyfingers with remaining orange juice; arrange over berries.
Gently stir the remaining confectioners’ sugar in the remaining whipped cream. Spread over ladyfingers. Top with remaining strawberries. Refrigerate until serving. If desired, drizzle with chocolate syrup before serving.