There is NO CONUNDRUM with Zechariah 14 except by those who refuse to believe that the Daniel 9:27 symbolic "one week" (70th) has not been fulfilled yet today.
The events in Zechariah 14 parallel the events for the end all throughout the New Testament Books. In particular, the two angels that appeared to Christ's Apostles at the Mount of Olives revealed Lord Jesus will return in like manner as He was seen ascending to Heaven from that Mount of Olives. The Zechariah 14 Scripture completes that picture, because it says Jesus' feet will touch down on the Mount of Olives at His future return.
But what has men's doctrines done with how Jesus returns? A good portion of deceived brethren think they are going to be raptured to heaven off the earth to live in the clouds above the earth, when that ain't gonna' happen. It is not written. That idea happened because of Biblically illiterate men trying to preach when God didn't call those. They are almost totally ignorant of how Apostle Philip was "caught up" and relocated to another place ON EARTH after he had witnessed to the Ethiopian in the chariot.
When Lord Jesus returns on the "last trump", those of us still alive on earth will be suddenly 'changed', casting off our flesh body with our "spiritual body" revealed, and then "caught up" to Jesus and the asleep saints He brings with Him on His way to.................... the Mount of Olives on earth. That Zechariah 14 Chapter simply completes that picture. Apostle Paul did not show exactly where... Christ's Church will be brought to after being "caught up", but Zechariah 14 does show it.
So when one hears of Christ Jesus gathering His faithful Church to any other place besides the Mount of Olives on earth, then you know they are pushing doctrines of men, and not staying with the actual Bible Scripture.