I would go with the small box only because I have seen other people's box's and I got more stuff then they did. I have a chihuahua and I usually get 2 toys(bouncy ball, squeaker, rope toy) 2 bags of treats and a few enzyme rawhides. I think you get more bang for your buck. The smallest toy I got was a bouncy ball that was the size of a golf ball. So you might not want to give that to your medium size dog.