Interesting puzzle.
Years ago, (I worked in the Aerospace Industry) we had to fill a void with epoxy to lock three legs together after a satellite dish was aligned (three places). Well, the "void" where the three legs were, was very small, and the epoxy was somewhat thick, thus, it was a difficult squeeze !
I was tasked with finding if an "angle", or a radius was better than a 90° squared off corner was where the epoxy had to pass.
LONG story short, a "radius" was..."marginally" better than a standard 90°, and no other angles changed the pressure required to force the epoxy into the void.
I doubt that "air" would be much different, especially when you look at the coefficient of drag on cars for the effect of air passing over the front of the car, dealing with streamlining. Which is basically the same situation you are talking about. The only way to reduce that drag is to make the car smaller, that is, narrower and or shorter (ground to the top).
So, in your situation, would be to make the larger diameter pin smaller, which...you can't do !
Your comment about "part of the pressure" is incorrect thinking. You aren't lessening the surface area, you are "only" moving into a different location.
Properly quantifying any improvements in your situation, would be a difficult, expensive task at best.
BUT...go for it, I'm never...one to stop someone from his (her) experimenting.
Mike