Graueradler's got it -- it's all about sectional density (mass divided by frontal area). As the size of a sphere increases, its weight goes up faster than its flat-plate area (weight being proportional to the cube of the linear dimension, while area is proportional only to the square of the linear dimension), thus increasing the velocity needed to create an amount of drag equal to the weight of the drop (drag being proportional to area times velocity-squared).
BTW, I suspect that the reason the group of smaller droplets can fall faster than a single droplet of the same size has to do with the same effects which allow "drafting" in racing -- that a pack of race cars can go faster than one car alone. It's all about changes in the airflow around the group compared to airflow around the single car, resulting in two cars running together having lower total drag than the sum of the drags of two individual cars.