Does ingrown toenail surgery usually hurt?

Yes: But probably no more than the pain you have from the ingrown toenail already. Away the surgery you are in a post operative shoe with a dressing on which does not put much pressure on the surgical site.

Not really: There is some discomfort from the injection to numb the toe.

Very minimal: You will feel a stick from the injection and some burning from the numbing medicine. After that the procedure is painless. After the numbing wears off, the area can be tender for the next couple of days which can be managed by tylenol (acetaminophen) or advil.