first I don't understand what you think the disciples are asking about when they say "when will this happen?" if it is not referring to the destruction of the temple that Jesus was talking about in Matt 24 verses 1 and 2.
but part is our different understanding of Daniel 9...
Daniel does NOT say the Future prince, but the PEOPLE of the future prince. there is a big difference. let us look at the key verse
Daniel 9
26 “ And after the sixty-two weeks
Messiah shall be cut off, but not for Himself; (Jesus cruxified)
And the people of the prince who is to come (romans and antichrist people)
Shall destroy the city and the sanctuary. (destruction of temple 70 AD)
The end of it shall be with a flood, (do you remember the verses in Revelation where Satan floods the woman and her children who have the testimony of Christ?)
And till the end of the war desolations are determined. (this would be Ammageddon)but the statement says the END of the War is determined meaning finding out who will win, this happened when Jesus defeated all powers and principalities at the cross
27 Then he shall confirm a covenant with many for one week; who is the HE?can God make more then one covenant? can He make it conditional?
But in the middle of the week
He shall bring an end to sacrifice and offering. Did not Jesus bring an end to sacrifice by giving HIS life as the only sacrifice needed?
And on the wing of abominations shall be one who makes desolate, sounds like the Whore Babylon
Even until the consummation, which is determined,
Is poured out on the desolate.”
why do I think the verses "on the wings of abominations" means Babylon?
well it fits with these verses:
Zechariah 5
5 Then the angel who talked with me came out and said to me, “Lift your eyes now, and see what this is that goes forth.”
6 So I asked, “What is it?” And he said, “It is a basket[a] that is going forth.”
He also said, “This is their resemblance throughout the earth: 7 Here is a lead disc lifted up, and this is a woman sitting inside the basket”; 8 then he said, “This is Wickedness!” And he thrust her down into the basket, and threw the lead cover over its mouth. 9 Then I raised my eyes and looked, and there were two women, coming with the wind in their wings; for they had wings like the wings of a stork, and they lifted up the basket between earth and heaven.
10 So I said to the angel who talked with me, “Where are they carrying the basket?”
11 And he said to me, “To build a house for it in the land of Shinar;[c] when it is ready, the basket will be set there on its base.”
shinar is another name for Babylon and the verses before talks about the curse upon the world, which would be desolate, as the world consummates their affair with the Whore.