You have set up a false argument here. The rapture does not correspond to the Israelites entering Canaan! It corresponds to God bringing destruction on the world!
Jesus himself said, "As it was IN THE DAYS OF NOAH..." (Matthew 24:37- ). And "As it was IN THE DAYS OF LOT..." (Luke 17:28- ). God is about to destroy the world by fire (2 Peter 3). Before He does so, the church will be removed to a place of safety.
There is still time to get into the church. Believe on the Lord Jesus Christ and you will be saved!
——>God is about to destroy the world by fire (2 Peter 3). **Before He does so, the church will be removed to a place of safety.**
No. The earth is destroyed by fire AFTER the millennium, the resurrection of the wicked, and of course that would mean AFTER the second coming of Christ. (The church is already safe at that point).
http://www.biblelightinfo.com/millen.htm