Actually, I think it happens BEFORE that. Perhaps the Battle of Gog/Magog... The Temple is rebuilt in Holiness... the whole of Jerusalem is sanctified - The bells on the horses and the jugs for the water have the name of YHWH upon them... All of this, according to the Prophets, happens when the Temple is rebuilt... And the Temple IS THERE for Yeshua to enter into through the Eastern Gate after His foot touches down on the mount of olives!
And if that is so, That allows a great portion of Judah to participate in the rapture - How can YHWH allow a part of Yeshua's Bride to ride the lightning? It seems it will be the Left Behind of both Christian and Jew (by then ONE THING) that will be the Tribulation Saints...
I know that is weird, but it works... and it puts the Rapture mid-trib... living through the time of Jacob's Trouble, enduring the Antichrist, but not the wrath of YHWH. All the saints are with Yeshua when He comes to deliver that, and establish the throne of David!
I have to go back and do some reading to respond to the rest of your post. I still believe the conversion of Israel will occur at His glorious return, but I'll try and give that some thought.
I think the mid trib rapture is not as likely in part because if the church is still present on the Earth it would negate the impact of the 144,000 witnesses and the outcry about prophesy being fulfilled would open peoples eyes.
Rom 2:4 Or despisest thou the riches of his goodness and forbearance and longsuffering; not knowing that the goodness of God leadeth thee to repentance?Can you think of any place where judgment led to repentance? I dont believe that tribulation or war will bring the conversion of Israel. If we consider the prophetic character of history in scripture, perhaps we should be looking for an event like Joseph reveling himself to his brothers. The details argue against a mid-tribulation rapture.
Amos 8:11 Behold, the days come, saith the Lord GOD, that I will send a famine in the land, not a famine of bread, nor a thirst for water, but of hearing the words of the LORD:Do you suppose the rapture will cause a spiritual famine?