I had this situation before, and while my players have not tried to try again after failing to sharpen their swords, I know what I would say:
The stake here, during this maintenance scene, is seeing how this seemingly innocent act of taking care of your weapon might impact your future. The stake of success is making the weapon repaired and possibly Durable; this might save your life ten days later, during a duel. The stake of failure is that you won't have this durable buff...and it might be the last straw that breaks your back.
Shall we roll?