Very good/nice question!
25;
"Know therefore and understand, that from the going forth of the commandment to restore and to build Jerusalem unto the Messiah the Prince shall be seven weeks, and threescore and two weeks: the street shall be built again, and the wall, even in troublous times.
26; "And after threescore and two weeks shall Messiah be cut off, but not for himself: and the people of the prince that shall come shall destroy the city and the sanctuary; and the end thereof shall be with a flood, and unto the end of the war desolations are determined."
Do you see this? "the people of the prince that shall come",
Then, who is it that this verse says it is "that shall come"?
It is
"the people of the prince" =
"that shall come" and do the destroying, not
"the prince".
"the people of the prince that shall come shall destroy the city and the sanctuary"; that is, the people of the Romans, under Vespasian their prince, emperor, and General Titus, who was Vespasion's son, should, in a little time after the cutting off of the Messiah at His Crucifixion, enter into the land of Judea, and destroy the city of Jerusalem, and the Temple that stood in it;
(though some understand this of Messiah the Prince that should Come in His Power, and in a way of Judgment upon the Jewish Nation, and destroy them for their Rejection and Murdering of Him and it is True in my belief, but not as the Primary Interpretation OF "THE PRINCE" but would be an application and we'd need to add a Capitol "P" in Prince then; Matthew 24: the "Coming of the Lord" that the Deciples ask Jesus about was when they thought Jesus might Make His Triupham Proclimation that He was taking over the Rule of the Government from The Jews, when they asked, "what shall be the sign of Thy Coming", in 24:3b, while the real question that Jesus Answered was concerning the signs there would be prior to Jesus Coming in Providential Judgment upon the Jews, with Him Overseeing The Roman Armies "in the clouds", like in the Old Testament and Matthew 24, because at that Time in 70 A.D. the people or the Roman Army would be under Jesus Direction, ultimately, and Jesus would also ultimately be the One by Whose Orders, all these Judgments would be brought upon the Jews, in Jerusalem, A.D. 70.
So, in Matthew 24 Jesus is the Primary Interpretation of Who was to do the destroying, by Using the people, the Roman Armies, was Jesus, as we see in 24:
27;
"For as the lightning cometh out of the east, and shineth even unto the west (when you realize the Roman Armies are Coming (as Jesus is Using them = you better ruuun!!); "so shall also the coming of the Son of man be" when Jesus' was Coming in Judgment against those Jews who as a Nation had Crucified Him). 28;
"For wheresoever the carcase is" (the deceased Jews), "there will the eagles" (the Roman Army who's insignia was an Eagle) "be gathered together", but here in Daniel 9, it is going to be Vespasion as the Primary Interpretation, being the actual historical prince at that time and his son, Titus, who carried out the Abomination of Desolation (Matthew 24:15). Many of the Jewish writers themselves Interpret it of Vespasian, as Aben Ezra, Jarchi, Abarbinel, and Jacchiades:"
"Gap" sounds strangely familiar. 70 years equalling 69 years plus approximately 2000+/- years plus 1 more year? Not your typical Prophecy accuracy we'd like to see.
The 2069th+/- week, plus one!(?)
"the people of the prince that shall come shall destroy the city and the sanctuary" is how it is said in Daniel 9:26 KJV. So, we have to make sure we're saying what's there right.
Yes, Vespasian can be the one talked about here and his son, Titus "for the overspreading of abominations he shall make it desolate", whereas the Determination was by Jesus' Decree, for sure.
Once you have Daniel, Matthew, and Revelation under your belt, where you feel very confident about your understanding of Daniel 7, Matthew 24, and Revelation 20:4, especially, you will be glad you stuck with them to get at least your weight in Gold regarding them.
If there are more difficult verses to interpret, while reconciling them among themselves and the rest of the Bible, I haven't met with them yet.
And having said that, I have certainly found allowing the Bible to interpret the Bible, to be unbelievably awesome and am amazed just how often we can benefit from doing that, especially in the most difficult and obscure passages, while under the Lordship of Jesus!
Speaking of rare, how often could we all Increase our Blessing in understanding what God would have us to know, the MORE WE PRAY about these "things of God"?
) I think I have already "gained the understanding" of the book, but I have doubts about you. 
(That was an offensive statement. Just saying, you know. It is impolite to assume ignorance in a debate opponent.)
