In Matthew 11:16, “this generation” could easily be referred to as the Jews as a people group, as does “the men of Nineveh shall rise in judgement with this generation”, which likely does denote people groups. I don’t find these things to be a logical squeeze at all. Are they the correct interpretations? Don’t know. What does the Holy Spirit tell you (1st John 2:27)?
Good advice to focus on what the Lord says. Now see if you can determine whether the things he describes in Matthew 24 have alread taken place.
As for me, I don’t go by “systematic theologies”. I only go by what I see.
I remember approaching a preacher with an obscure piece of Scripture and asking him what it meant. He asked me, “Are you going to live that passage today?”
I answered with another question, “How can I live it if I don’t even know what it means?”
He replied with the best answer I’ve ever gotten to such a question. “Well, there’s plenty enough in the Scripture that you can plainly understand. Why don’t you work on living those things. Maybe if you’re successful at that, the Lord will reveal to you what these more difficult passages mean.”
So have you gotten beyond the Sermon on the Mount? I mean, it’s pretty plain and easily understandable. If you’ve gotten all that right, then you’re a much better Christian than I am.
There was only one chronological generation of Nineveh that heard the preaching of Jonah, just as there was only one chronological generation of Israel what was personally preached to by the Lord Jesus Christ. The parallel Jesus was making is unmistakable and renders your alternative interpretation unsupportable.
You have to deny the plain words of the Bible to come to some other conclusion on the meaning of this generation.
The Jews are not an evil people group, which is the way you are forced to interpret Matt. 12:39.