Sasuke has come pretty close actually. As an adult, he thinks more rationally and has even implemented some of Itachi's teachings in one way or another. For instance, during that arc with that mysterious doujutsu, Sasuke showed a calm demeanour and was even better at reading social clues.
Ultimately, Itachi was always more insightful and quick to adapt, whereas Sasuke still remains to be dense sometimes.
I would say, given the time he's had to grow as a character, he's definitely surpassed him in most respects, but sagacity is definitely not one of them. Itachi's wisdom was vast.
