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I usually drill undersize, and then use a chucking reamer to ream it to exact size. A round file will probably make the hole even more oblong, unless you have EXTREMELY steady hands...
knives and pics look great!!!! Great use of DOF as well....
Great job Shannon! Keep up the good work.
I personally drill my pin holes to size. Generally speaking my micarta pin stock is a little oversized so I chuck it in a drill and hit it with some coarse sand paper and test fit it until it just slides in. Then I make sure I roll it in the epoxy before pushing it through the handles. I have not had any with gaps quite like that though so you may want to check the actual size of the drill bit and the pin stock.
You can also fix those gaps you have with some thick CA glue. Just fill the hole and sand it down. With the black you will probably never be able to see it ever had a gap.
Haha! Sorry about that... tell you to ream without telling you how
http://usaknifemaker.com/drills-taps-saw-blades-c-98.html#p=1&gan_data=true
The cheaper HSS ones are just dandy for handle material (even for folder pivots providing the blade isn't hardened)