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You're actually making my point for me. The Bible consistently speaks to future generations in a present tense quite frequently--and this literary trait does not simply vanish in the NT. Therefore, when you consider a statement like, "this generation," you cannot rule out the possibility that:

a) "this generation" refers to the generation that would see the events described in the Olivet Discourse, which could be far in the future,

b) "this generation" refers to "this people," which is a perfectly acceptable translation of the Greek genea, or

c) as in Moses' prophecy, multiple fulfillments are in view.

The last option is the one that I accept, on the basis that that's simply how Biblical prophecy works. Take the Immanuel prophecy, for example: First, the prophecy is about a sign to Ahaz, not something that wouldn't be seen for 700 years. Second, the child is supposed to be too young to know right from wrong when the fulfillment comes, not unborn for 700 years. Third, the fulfillment of the prophecy is arguably given in the very next chapter (ch. 8) of the book.

So why then do we accept Matthew's exegesis of the passage as Messianic? Because there are unfulfilled details and loopholes in the "time" statements that lend it to that interpretation: First, there is no definition of the Hebrew word 'almah that fits Isaiah's wife, since she had already had a son who was old enough to accompany Isaiah when he went to speak to the king. Second, the child is supposed to be called Emmanu'El, not Maher-Shalal-Hash-Baz, as Isaiah's son was named in chapter 8. Third, the passage does not end in chapter 8, but goes on to describe the Messiah in chapter 9, still speaking of the "the Child [who] is born . . . the Son [who] is given."

Matthew, inspired by the Spirit and seeking to understand the Virgin Birth in light of the prophecies of the Tanakh, saw the fine details of this passage fitting perfectly with Yeshua's birth and destiny. The time-statements of the passage did not bother him because a) Isaiah offered the ultimate fulfillment of this sign not just to Ahaz but to the whole House of David, and b) while it truly is a loophole, a child who is unborn is too young to know good and evil.

In the same way, I fully believe that the destruction of the Temple in 70 AD is within the scope of the Olivet Discourse. Indeed, I believe that Luke intentionally paraphrased the Lord's prophecy to bring out that aspect of it (a practice that was perfectly acceptable by the standards of the day). However, there remain fine details of the prophecy that have never been fulfilled:

1) Titus did not set up the Abomination of Desolation in the Holy Place the way that Antiochus did or that Paul described in 2Th. 2:4.

2) "All flesh" was never at risk in 70 AD. The Romans knew that the rebellion was being driven by a minority of the Jews, primarily the Zealots, and had no problem with Rabbi Yochanan ben Zakkai establishing an academy in Yavneh in order to ensure the survival of Judaism as a religion. They didn't really crack down on Judaism as a whole until the Bar-Kochba revolt.

3) The Lord's Coming--and yes, He did come in a spiritual sense in judgment--was neither visible to those who pierced Him, nor was it accompanied by the gathering of the Elect into the clouds nor by the Resurrection of the Dead as Paul anticipated (1Th 4:15ff, 2Th 2:1ff).

Since just as in Isaiah's prophecy, there are these little details that don't quite fit, while I agree that there was a fulfillment of the Olivet Discourse in 70 AD, I also anticipate a future fulfillment where, just as in the Immanuel prophecy, those details will be fulfilled more literally.

We like to think of it as expansion, not replacement, since the children of Israel have always been an integral part of the expanded kingdom of God, which now is made up of all the nations.

You're so close to the truth. Where we disagree is on what it means that "all Israel will be saved."

Shalom!

However, the phrase "this generation" as we find it in Matthew 24 and Luke 21 is unlike anything you quoted in those passages from Deuteronomy. "You and your descendent" does not mean a single generation as I pointed out. And neither it nor "this generation" carries some mythical multiple fulfillments.

Of course you also fail to see that Deuteronomy is not a prophecy, but language flowing from the giving of the Law. It is a statement of conditions; do this and be blessed, don’t do this and be cursed. It is part of God’s legal code; conditions of the covenant. The choice was before Israel. There is no language of predication of events that must happen by necessity.

By way of contrast, there is no conditional language ala Deut. 30 in Matthew 24 or Luke 21. It is a prophecy (prediction) of what will be.

In fact, if you wished you could find similar language in the OT to see its meaning. E.g.,: "Surely not one of these men of this evil generation shall see that good land of which I swore to give to your fathers," (Deut. 1:35, cf. Gen. 7:1)

A specific generation was in view, the one that failed to enter into the promised land because of their sin. They wandered for 40 years until "this generation" eventually died off.

Then of course there are all the other places in the NT where the phrase is plainly referring to the contemporary 1st century generation (cf. Matt. 12:41).

However, there remain fine details of the prophecy that have never been fulfilled:

That is a matter of debate based on interpretative principles. It can only be said that the prophecy has not been fulfilled it one requires an unnecessarily literal interpretation of the text, or confuses those portions which are near in view vs. those which are more distant. Again, reading the time text is critical to a proper interpretation.

You're so close to the truth. Where we disagree is on what it means that "all Israel will be saved."

Interesting. How can you be sure? I don’t believe you have ever said what you believe it means.