Point 1 - Let Daniel 9:25 refer to the complete rebuilding of all Jerusalem, not just the Temple. This places the "decree" in 445/4 BC, not 539/8 BC, on which, see point 2. (Also see notes below. Liberals may attack this point first but I claim it as my premise and simply ask - if we accept this as given, what proceeds logically from here?)
Point 2 - Instead of doing arcane mathematical gymnastics, as some have done, count inclusively. The first "week" does not begin on the moment the decree was given. The first week is already on the calendar! It's the week during which Artaxerxes (in 445/4) gave Nehemiah permission to rebuild the wall. Those seven years ran from Autumn 450 to Autumn 443 (by Zuckerman's reckoning).
Point 3 - Proceed directly and sequentially from this first "week" to the 69th. That seven year period begins in Autumn 27 AD and runs until Autumn 34 AD. (Note the Math: 450 + 34 = 484 yrs = (69 * 7) +1, where the plus one disapears when restricting the count from Autumn to Autumn, giving the accurate total of 483.) Significantly, this week encapsulates the entire ministries of both John the Baptist and Jesus.
Point 4 - Just as the decree of Artaxerxes did not begin a strict countdown of 483 chronological years, the crucifixion of Jesus (April, 33 AD) does not have to come at the 69th week's precise end (which, in any year, would be in Autumn, not Spring).
Point 5 - Anyone taking Wacholder's years (as opposed to Zuckerman's) should not find any trouble in working with the above points, but - while I'm on the subject - let me say I personally find it much more significant, theologically, that Christ laid up his propitiation for all time in the Year of Preparation, before the Year of Rest (and likely the Jubilee, too.)
Notes: I'm not an O.T. or ANE guy, and I'm doing this strictly for the NT application - so much of my Persian history research (and all of 'my' Hebrew interpretation of Daniel 9:25) is borrowed from Harold Hoehner's generally excellent and thoroughly researched Chronological Aspects of the Life of Christ (Chapter 6). However, one of the few criticisms I hold of this fine, classically trained scholar is that he calculated the numbers according to "prophetic months". Therefore Point 2, above, is my own added twist. Mathematics, like historical theories, is best when done simply.
Incidentally, I did actually tuck all this into a summary piece I did in 2006, which I'll now excerpt here. Pay attention, old friends - Jesus shows up at the end! :)
In 539 BC, the year that Daniel met Gabriel, the Kingdom of Persia conquered Babylon. It was also the year Daniel saw a vision of the rebuilding and the future re-destruction of Jerusalem.
In 538 BC - the following year, Cyrus, King of Persia, let many Jews go back to Jerusalem. Cyrus let Zerubbabel and the Jews rebuilt their temple, but not the walls.
In 480 BC - Xerxes, King of Persia, killed
300lots of Spartans at Thermopylae, but lost the war against Greece. Back home in Persia, three years later, he married a Jewish wife, named Esther. She comforted him, after his loss.
In 458 BC - Artaxerxes, King of Persia, let a Jewish man named Ezra lead a new group of exiles back to Jerusalem. Ezra read the law, and the people decided to follow it. That autumn, they dedicated the next twelve months (and every 7th year after) as a Resting-Year to the Lord.(It just so happens that, about this time, a Greek named Pericles was leading Athens into their famous "Golden Age".)
In 445 BC - Artaxerxes decided to let Ezra and Nehemiah rebuild their whole city, and even the walls of Jerusalem. He gave this decree mid-way through one of Israel's 7-year cycles.(That cycle - when the walls were rebuilt - was the first cycle out of 69 cycles that Gabriel told Daniel about. The 64th cycle is when Jesus gets born. The 69th cycle is when Jesus does his work.)