I'll try and take this on for the time being. Maybe I can try and address some of your other points at a later time, but no promises though.
Here's an article I found that can explain my position better than I can. It's not a lengthy article if you care to read it. I know very little about this site, so not endorsing it one way or the other. Only providing an article I found via searching Google that tends to explain some of my position better than I could. You have two choices. Either you can consider some of these things or you can choose to be closed-minded about some of these things instead. Your choice.
Here is an excerpt towards the end of the article----
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Since Daniel’s prophecy directly quotes the words of the angel Gabriel, is it wise to assume that the sanctuary in verse 26 is a temple made with human hands, one that was merely a shadow and a type of the real one? The tabernacle in the wilderness was made according to the pattern of heavenly things. [Hebrews 8:1-6] Similarly, the temple of Solomon, and the temple of Zerubbabel, built after the Jews returned from exile, were built after the same pattern, and so were “shadows” of things heavenly, and spiritual. What sanctuary, then, is meant in the message of the angel in Daniel’s prophecy?
In the angel’s words, “after threescore and two weeks shall Messiah be cut off, but not for himself,” for whom was he cut off? Isaiah wrote: “But he was wounded for our transgressions, he was bruised for our iniquities: the chastisement of our peace was upon him; and with his stripes we are healed.” [Isaiah 53:5]
The New Testament identifies both the “city” and the “sanctuary,” (or temple) with the church, those for whom Christ was cut off. In verse 26, where the “city” and the “sanctuary” are destroyed by the people of the prince that shall come. This must refer to the real sanctuary, rather than its type, or shadow. Applying the words of the angel to the shadow misses the true significance of the prophecy. Why would an angel of God have been sent to reveal the future destruction of a mere shadow, or a type, that in Daniel’s time had not yet been built? The real sanctuary is the church.
Daniel said of the prince, who opposes the Prince of princes, “And his power shall be mighty, but not by his own power: and he shall destroy wonderfully, and shall prosper, and practise, and shall destroy the mighty and the holy people.” [Daniel 8:25]
The saints are the “sanctuary” described in Daniel’s prophecy. The Jewish temple, made with hands, was destroyed in 70 AD, but no flood was involved. Its destruction has obscured the significance of Daniel’s prophecy. The desolation of the church, however, has an immense significance for our understanding of the gospel and the history of church.
Each of the things that were to be accomplished within the 70 weeks, mentioned in verse 24, pertain to the gospel. This fits the view that the temple and city that Daniels’ 70 weeks apply to is the church, of which the earthly city and temple were types and figures. The atonement and forgiveness of sin, bringing in of everlasting righteousness, etc., are accomplished in the last week, after the coming of the Messiah. Auberlen recognized that everything mentioned in this verse have to do with the gospel. He wrote: [5]
https://creationconcept.wordpress.com/2011/09/11/which-temple-is-meant-in-daniel-926-27/
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BTW, I just found this article. So I didn't form my understanding because of this article, but that this article tends to explain my understanding of some of these things better than I could.
To add to the above, there is also the following to consider. The following is solely my attempt at trying to explain my understanding of some of these things.
Daniel 8:24 And his power shall be mighty, but not by his own power: and he shall destroy wonderfully, and shall prosper, and practise, and shall destroy the mighty and the holy people.
If the city is perhaps meaning the holy people, this text indicates this---and shall destroy the mighty and the holy people.
The Hebrew word is shachath. It is found in 4 passages in the book of Daniel. In the first passage below it was translated 'corrupting'. The others it was translated 'destroy'.
Daniel 11:17 He shall also set his face to enter with the strength of his whole kingdom, and upright ones with him; thus shall he do: and he shall give him the daughter of women, corrupting her: but she shall not stand on his side, neither be for him.
Daniel 8:24 And his power shall be mighty, but not by his own power: and he shall destroy wonderfully, and shall prosper, and practise, and shall destroy the mighty and the holy people.
25 And through his policy also he shall cause craft to prosper in his hand; and he shall magnify himself in his heart, and by peace shall destroy many: he shall also stand up against the Prince of princes; but he shall be broken without hand.
Daniel 9:26 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.
Destroy doesn't have to always mean as in the demolation of literal buildings, even when it seems to be meaning that---as in Daniel 9:26b.
Isaiah 62:10 Go through, go through the gates; prepare ye the way of the people; cast up, cast up the highway; gather out the stones; lift up a standard for the people.
11 Behold, the LORD hath proclaimed unto the end of the world, Say ye to the daughter of Zion, Behold, thy salvation cometh; behold, his reward is with him, and his work before him.
12 And they shall call them, The holy people, The redeemed of the LORD: and thou shalt be called, Sought out, A city not forsaken.
This passage says---And they shall call them, The holy people---A city not forsaken.
BTW as well, this doesn't mean I necessarily fully agree with every single thing per the article above. But I do agree with most of it anyway, for the most part.