Mix the raspberries with 2 tablespoons of the sugar and simmer until they release their juices but do not fall apart. Strain the raspberries to remove any seeds.
Place half of the pound cake on the bottom of a glass serving dish with a flat bottom. Sprinkle with half of the sherry and evenly spread with half of the raspberries. Top with the remaining pound cake, sprinkle with the remaining sherry, and spread evenly with the preserves. Set aside.
Whip the cream in a chilled bowl until it stands in soft peaks. Refrigerate.
Beat the egg yolks with the remaining 1/4 cup sugar until light and pale yellow, using an electric mixer. Bring the milk and vanilla to a boil in a saucepan. Remove the milk from the heat and slowly incorporate the egg yolks while stirring constantly. Continue beating the mixture over very low heat until the custard thickens but do not boil it.
Fill a large bowl with ice water and set aside.
Dissolve the gelatin in 1/4 cup cold water and stir it into the custard. Remove the pan from the heat immediately and set it in the bowl of ice water. Stir constantly while the custard is cooling. When it starts to set, fold in the whipped cream.
Spread the remaining raspberries on the preserves and spread with half of the custard. Sprinkle the macaroons over it and top with the rest of the custard. Chill for several hours until set.