There is a belief that the attacks were timed to coincide with the destruction of the Muslim Ottoman army at the gates of Vienna in 1683.
The actual engagement happened on the 12th, not the 11th, but that day began the nearly unbroken series of military defeats suffered by the Ottomans (whose Sultan was the Caliph of Islam, let us remember--the position some say Osama aspired to) culminating in the absolute prostration of the Islamic world in 1917, when the Arab world was colonized by the European powers and the Balfour Declaration brought the Jews back to the Holy Land.
Staying with the thought, I think it's possible that for Bin Laden, September 11, 1683--when the Ottoman army was still besieging Vienna and held the city at bay--represented the last time Islam was feared by the West.
We may never know the truth about this, though.
I never understood though, why the Muslims would choose an anniversary based on the Western calendar. If they wanted to select an anniversary date, wouldn't it be in the Islamic calendar?