Toss the strawberries with 2 tablespoons of the sugar and let sit for 20 minutes. The berries will begin to release some of their juices. Meanwhile, heat the vinegar in a heavy-bottomed 1-quart saucepan over medium-high heat until reduced by one-third and thickened enough to coat the back of a spoon, 10 to 12 minutes. Reduce the heat to low, and stir in the remaining 3 tablespoons sugar until dissolved. Remove from the heat and let cool briefly.
Whip the cream with a hand mixer to very soft peaks that barely hold their shape.
Serve the strawberries and their juices in bowls drizzled with the balsamic syrup and topped with dollops of whipped cream.
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