Naruto would get owned by Itachi no question at all, but not because Itachi doesn't have to do anything. If Itachi's a genjutsu user, then he expect he should be expected to use that. And keep in mind we really don't know how strong Naruto's gotten, and neither does Itachi, so he's playing no games. One more thing, the description of genjutsu just answered a debate I remember being a part of a while back about how genjutsu works. On one opponent at a time. So that total darkness spell used in the kage fight only affected Sandaime.

Edit to below: It wasn't fear that made him cry, it was the emotions brought up by the visions, mainly guilt and feelings of inadequacy.