No Not Too Green

I have started on the nail holes but everything I do seems to close them back up. What size pin do you use in your vise and at what 'point' in the process. Should I wait until after the walls are stained and mostly weathered? Or is there a reason for now?

You know sitting 10' away from my green monster it doesn't look so bad. Maybe, all my close-up work and pictures over-emphasize the green.