Posted an E-mail on the Van's Air Force forum about my botched countersink and recieved confirmation that I needed to reorder the striker plates. It's Sunday so I'll call first thing Monday as this particular part (R-1007) is not on the "List" so I can't order it online. Drove on with match drilling the skeleton as the striker paltes didn't impact the rest of the rudder steps. Finished up this session by removing the palstic on the rudder skins in prep for match drilling them to the frame.
Figured out the cause of the bad CSK's was from the microstop falling off the plates during the machining process. Next time I'll mount it in the drill press to avoid that problem.