I still wasn't so sure if the flight would work out, the weather was marginal, or right on the edge. When we had to make the decision around 3:30 pm as to if I would head out to the airport, but things didn't look so good. At the time, the visibility and winds were fine, but there was a broken layer of clouds at both 3,500ft and 4,100ft. In addition, there was a dissipating storm moving towards Richmond from Charlottesville (we weren't 100% sure when/where it would completely dissipate). Because of this, we ended up making the decision to cancel the flight today.
Here is a photo of the forecast from today: as you can see, the weather was improving, but was on the edge of being un-flyable for me: