Ok so I could totally make fun of this guy, but I think he is really sincere about his belief. He was wrong in September 1994, so this takes a lot of guts to be wrong again. And yes I think he will be wrong again. Let me quickly unpack rapture and the end times (don't leave my blog please).
Rapture: a thought that before the end of the world and judgement of God Jesus will come back and take a select people who have followed his way correctly.
End times: there are three main views and only two of them are really being thought of today
Postmillenialism: The thought that Jesus will return after a prosperous time on earth and the reign of that time would be a literal 1000 years. This view was widely held in America following the revolution, but quickly dissipated when the American Civil War occurred. Obviously the idea of prosperity and a "Golden Age" didn't match the horrid reality of civil war
Premillenialism: The thought that Jesus will return and then there will be a 1000 years of torment giving those left from the rapture a second chance. This one cannot be easily defined since there are several branches of this one theory. I would suggest wikipedia as quick source. This view is widely held by many denominations.
Amillenialsim: The thought that Revelation 20 (which all of these are based upon) is not a literal description of when the end will occur. This thought believes more in the end coming without our knowledge and that judgement will occur immediately rather than any kind of literal 1000 year reign.
My tradition, Churches of Christ, have held mostly to Postmillenialism (pre-Civil War) and Amillenialism (today).
Now about tomorrow. I have a wee-ball game with my boys and I need to mow the lawn. If Jesus does come back at 6pm tomorrow, 1) I am ready to meet my Lord and 2) I will regret mowing (since it is my most hated task).