hch,
This Obama obsession is making you sound a little weird. Obama is DONE! Trump is in charge now. If anything happens to him, Pence will become president. If anything happens to Pence, Paul Ryan will become president. If anything happens to Ryan, Orrin Hatch becomes President. If anything happens to Hatch, Rex Tillerson becomes president. (from Wikipedia). Obama is nowhere in the line-up. It would take a coup or a revolution to put Obama back in office.
While we all dream up what scenarios on what we think eschatology says, the fact is, we don't know how prophecy will unfold. For example, my favorite "beast/antichrist" is radical Islam; but I could be wrong. I believe prophecy (especially eschatology) we written cryptically on purpose by God as to not disclose His plans to rebellious spirits and their human followers. There was no way the average Israelite or demon could foresee a suffering, dying Messiah until it happened. I Cor 2:7-9 says:
"No, we declare God’s wisdom, a mystery that has been hidden and that God destined for our glory before time began. None of the rulers of this age understood it, for if they had, they would not have crucified the Lord of glory. 9 However, as it is written:
“What no eye has seen, what no ear has heard, and what no human mind has conceived”— the things God has prepared for those who love him—"
The "rulers of this age" does not refer to the Romans and Jews, it refers to satan and his demons. If they knew killing Jesus would ensure His victory and their eternal doom, They would have never spurred the crowd to crucify Christ. If beings that are orders of magnitude more intelligent than us can't figure it out, do you really think we can? It's easy to infer from scriptures like Rev. 3:3 that we indeed will not know when and how Jesus comes until it happens:
"Remember, therefore, what you have received and heard; hold it fast, and repent. But if you do not wake up, I will come like a thief, and you will not know at what time I will come to you."
The bottom line is that one day sooner or later (sooner I hope) by a way we may or may not have conceived, Jesus will return to redeem his chosen and elect; and the Israelite Davidic Kingdom - with Jesus on the throne - will rule from Jerusalem.