I know this isn't the "preferred" approach, but I've turned pin removal and replacement into a two-person job ... and it becomes a snap.
To disassemble my R-9, I hold the pistol and pull back the slide. My wife uses a q-tip stick to push out the pin.
To reassemble it, I pull back the slide until I can see "air" through the larger hole (port side of the pistol) and she reinserts the pin.
As it happens, we performed two complete cycles today: I lubed the gun before visiting the range and cleaned it afterward.