I attempted about 100 photos of it but the bird was always in the wrong place at the wrong time. During the failed attempts of getting the right photo I ended up doing something different altogether; studying the caching behavior of Red-headed Woodpeckers.
I made an informal count of 40 trips of this bird flying from one side of the road to the other side of the road. After a while I realized it was collecting food (mostly acorns) and then caching it in a dead tree. Afterwards I googled and found out that Red-headed Woodpeckers are known to do this.
I wasn't thrilled about getting crappy photos in the wrong county but getting a first hand look at the caching behavior of a Red-headed Woodpecker made it feel as like it was time well-spent.