Hey Adam,
Here is my initial design direction, given the fact that you handle both baseball and softball: #15
As I mentioned in my comment, I am still open to implementing an actual double play silhouette. I just haven't finished it yet. Also, there is something nice about the simplicity of this compared to having them included.
Feel free to comment on this version, but I will try and get others posted soon as well. Most notably, one that does indeed include someone turning two.
I look forward to working with you on this, as baseball logos are always my favorite ventures to tackle here! P.S. - I love the name.