Rav Yoel Schwartz on 5761
Hebrewbooks.org just recently added a 52-page book by Rav Yoel Schwartz on the year 5761, which can be found here. It appears to have been written before 9/11, so it doesn't reference that monumental event, but it nevertheless has very interesting information.
First, he expands on the idea of the obligation to contemplate world events starting on p. 5.
He then summarizes the statements from various rabbis about the year 5760 and why they didn't pan out.
Next, he goes through various events that occurred in 5760 and 5761 and analyzes each one.
Finally, there is an appendix which compares the Oslo Accords with the Sin of the Golden Calf.
Update: There is another great book by Rav Schwartz also recently added that was written in 1980 - התקופה ומשמעותה - that talks about End of Days issues back then. The last half of the book (starting on p. 21) talks about 37 practical things we can do to help bring the Geula closer.