The temple was rebuilt.
The Messiah did come.
The Messiah was killed.
The temple was destroyed.
A ten year old could understand Daniel 9:25-26.
I can understand that people like to obfuscate because the implications of these prophecies having been fulfilled are tremendous. Daniel was definitely B.C. so the dating of Daniel doesn't come into it. By the way, did the sceptre depart from Judah when Shiloh came? Yes. Another related fulfilment of prophecy.
Well the dating of Daniel does come into it, since glossing over the fact that it doesn't actually date from the time of Daniel, and that it provenance is unknown, doesn't exactly inspire confidence in the content - I can see why some may seek to skirt round this inconvenient fact but they are only fooling themselves if they do.
Daniel 9:25-26 says this (NIV)
“Know and understand this: From the time the word goes out to restore and rebuild Jerusalem until the Anointed One,[f] the ruler, comes, there will be seven ‘sevens,’ and sixty-two ‘sevens.’ It will be rebuilt with streets and a trench, but in times of trouble. 26 After the sixty-two ‘sevens,’ the Anointed One will be put to death and will have nothing.[g] The people of the ruler who will come will destroy the city and the sanctuary. The end will come like a flood: War will continue until the end, and desolations have been decreed.
Yet is seems, according the link I provided earlier, that the
'seven ‘sevens,’ and sixty-two ‘sevens' isn't exactly precise since their are different views of what this means among Christians and the language (as translated in the NIV) isn't exactly clear and precise.
So, we get creative interpretation (theology) in order to claim it means something - but whether this something is justified by knowledge is another matter entirely given the imprecision inherent in the text.
I suspect you are taking the Bible too literally (and seriously).