In a small shallow casserole dish, toss the strawberries with vinegar and let stand at room temperature for 15 to 20 minutes. After the strawberries have marinated, check for sweetness, adding sugar if desired.
In a large bowl using an electric mixer, whisk the cream to soft peaks. Add the vanilla and confectioners' sugar. Whip until stiff peaks. Set aside.
Using a serrated knife, slice pound cake lengthwise into 1/2-inch thick slices. You will only need 4 slices. Using a 2-inch cookie cutter, cut out circles from each cake slice. Line up 2 high ball glasses and place 1 cake circle in the bottom of each. Brush 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 remaining cake, cream and strawberries to create a more humble trifle dish.
Cover 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 plastic wrap. Grate amaretto cookie on top and sprinkle with demerara sugar.