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|Devil's in the details
The single biggest question concerning the Second Coming is "what the fuck's taking so long?" The earliest Christians believed that Jesus' second coming was imminent, a view that seems to have been held by Jesus himself: in the Bible he tells a group of listeners that they will still be alive when the event takes place. Paul also seems to think that this will take place when some of his current followers (and himself) are still alive.
Some Christians argue that Jesus had limited knowledge in his human form and screwed up. This runs contrary to the widespread Christian belief that Jesus was both fully God and fully human. This also leads to another problem: how many of Jesus' teachings are in error? Complex attempts at apologetics have tried to explain this failed prophecy, however, using Occam's Razor, the simplest and most plausible explanation is that Jesus or whomever wrote that account predicted something that never happened. Certainly the early disciples expected Jesus to return during their lifetimes and Jesus was either not omniscient and overlooked this misunderstanding or knowingly deceived his own disciples. Others argue that when Jesus said "Kingdom" he was actually talking about the Transfiguration instead. Even so, it's scripturally irresponsible to suggest he didn't really mean what he said.
Second Peter (written many years after Paul's epistles) addresses the issue by saying a thousand years to God is but a day to him. By this logic, this millennium is the third day since the crucifixion. We're still waiting. Although this reasoning has led some literalists to assume that the Universe was created over the course of only 6,000 years.
Some preachers have made startling predictions regarding the second coming. Some notable examples include William Miller's great disappointment of 1844, the Jehovah's Witnesses prediction of 1914, and Harold Camping's most recent prediction on May 21, 2011.