Nice job Brian,
You definitely paid attention to Dave's instructions!
Files are what the fist knives a guy makes should be made from! ;~)
It does present a couple problems though. Files are a water hardened steels that are as hard as they can be. Usually 62-64 Rockwell C scale and brittle as glass. Kind of makes drilling a real pain, as you've discovered.
You may already know this, but I'll say it for the guys who haven't run into it before. For the next one you can get around the problem by using a simple propane torch. Just heat the tang, starting at the hilt end and chase the heat up the tang until it reaches the spine of the blade. Quickly stick just the edge portion of the blade in water or heat it with just the edge suspended in water. Let the tang cool to room temp with the edge in water.
The steel will turn several colors as it heats. If you heat it till it goes thru the blues to brown or wheat colors it should soften the steel to about 40-45 Rc. Not soft, but a lot easier to drill. Even with the so called carbide bits. Plus it makes the steel tougher. It takes the brittle out of it.
Just be careful not to get the cutting edge past the blue or purple color it was when you tempered it. Don't want that edge to get too soft and that is the color of about 56-58 Rc.
Again, great work. That's gonna be a perfect little pack knife! And the scabbard looks great too. Very tasteful, classic package.
Good work!