One of the critical things is what exactly does the word “until” mean? Is it definitive or is it conditional upon the Jews first believing and then Jesus returns?
I think the prophecies were older than that. But either way it’s not a big deal. To me.
In Genesis 3 , i believe was the prophecy between “the seed of the women” and Satan was 3,500 years in advance! What does the bible say a thousand years to God is?
I appreciate that this prophecy would appear to be conditional, but we see this earlier related unconditional prophecy regarding the certainty of the Jews’ repentance at the Second Coming…
Zec. 12:9-10
9 On that day I will set out to destroy all the nations that attack Jerusalem.
10 “And I will pour out on the house of David and the inhabitants of Jerusalem a spirit of grace and supplication. They will look on me, the one they have pierced, and they WILL mourn for him as one mourns for an only child, and grieve bitterly for him as one grieves for a firstborn son.
…later being interpreted with unconditional certainty in this way:
Rom. 11:25-26
25 I do not want you to be ignorant of this mystery, brothers and sisters, so that you may not be conceited: Israel has experienced a hardening in part until the full number of the Gentiles has come in,
26 and in this way ALL Israel will be saved. As it is written: “The deliverer will come from Zion; he WILL turn godlessness away from Jacob.”
So Hermano, You don’t see the Jews returning to Israel first in unbelief as a problem?
It is a step-by-step process of repentance for the Jews, directed by a patient God, which will finally result in incomparably greater blessings for them than ever before.
A two-part series on open theism from Restitutio. Should be very provocative.
https://restitutio.org/2019/12/05/303-foreknowledge-and-freewill-1-dale-tuggy-introducing-open-theism/
https://restitutio.org/2019/12/12/304-foreknowledge-and-freewill-2-dale-tuggy-defending-open-theism/
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Well… I held my view of the matter long before I discovered that view to be “open theism.”
In brief, I believe that God is omniscient. But being omniscient does not imply that He knows that which cannot logically be known, namely what a free-will agent will choose in the future.
There are plenty of matters that God does not know in the impossible sense. For example, He does not know that the moon is made of green cheese. Simply because it isn’t. Similarly, He cannot know what a free-will agent will choose. Simply because the agent has not yet made that choice.
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In Oregon we say “If you don’t like the weather, wait 10 minutes, it’ll change.”
I’m much more stable than that - it takes almost a half-hour for me to change my mind on divine foreknowledge. 
As of now, I believe God can determine the future, but doesn’t micro-manage it. Freedom of the creature is maintained within limits.
Basically, our choices do count, our characters do matter, and God does determine the outcome. I don’t see any way for me personally to go much further than that, even though conceptual problems remain.
How about you?