As far as multiple entries, I'm only going to count one entry per month. (Otherwise, we could have one shooter win 1st, 2nd, and 3rd.) I think we will add an Expansion Era class, though.
I may address this again in the future, but for now we'll stick with one. (You all may have noticed this is still evolving. You never know, I may be able to talk the General into letting this count towards earning your GAF Marksmanship Medal........)