For the marinated strawberries: In a small, shallow casserole dish, toss the strawberries with the vinegar and let stand at room temperature for 15 to 20 minutes. After the strawberries have marinated, check for sweetness, adding sugar if desired.
For the whipped cream: In a large bowl, using an electric mixer, whisk the cream to soft peaks. Add the vanilla and confectioners' sugar. Whip to stiff peaks. Set aside.
For the trifle: Using a serrated knife, slice the pound cake lengthwise into 1/2-inch-thick slices. You will only need four slices. Using a 2-inch cookie cutter, cut out circles from each cake slice. Line up two highball glasses and place one cake circle in the bottom of each. Brush the cakes with amaretto liqueur. Add 2 tablespoons of marinated strawberries and spread evenly. Using a different tablespoon, add a large dollop of whipped cream and spread evenly. Add a second layer of cake, pressing down lightly. Brush with amaretto liqueur. Add 2 tablespoons of marinated strawberries and spread evenly. Top with a large dollop of whipped cream, spreading evenly. Use the remaining cake, cream and strawberries to create a more humble trifle dish.
Cover the trifles with plastic wrap and refrigerate for impromptu indulgence, keeping in mind that it will store for up to 2 days.
To serve, remove and discard the plastic wrap. Grate some amaretto cookie on top of the trifles and sprinkle with Demerara sugar.