This can be obtained by shooting the tires on any cars. Moving cars and parked cars.
You can only shoot 1 tire per car, so shooting all 4 tires on the same car, only counts as 1 towards the achievement.
The best place I can recommend is a multi-storey car park/parking lot and you should be able to get a good number of cars without alerting any civilians/police. (Use a silenced weapon for best results)
Otherwise, you can run out into a busy street and just shoot any cars you see. Although this can negatively impact your reputation.