To touch up on the not being able to repair issue. I should have noted that this is a Dedicated Server / Multiplayer environment. I unloaded all plugins to see if any would be the culprit but none were. I cannot repair any tools in multiplayer via dedicated server at all.
When in the worn state, the bottom left tooltip doesn't show anything and states it is already sharpened on right click.
The only way a tool will show the repair tooltip on lower left side, is if it's broken.
Drill will not repair, nothing does in multiplayer. Assuming this is a multiplayer only bug.