I would love to see a timeline of when you think Jesus said what. In other words, I'd like to see you combine Matthew 24 and Luke 21 together to show when you think He said what He did in Luke 21:20-24 and when He said what He did in Matthew 24:15-22.
It's obvious to me that He said what He did as recorded in Matthew 24:15-22 (and Mark 13:14-20) only once and Luke paraphrased what He said for the benefit of his Gentile audience. So, instead of saying when you see the abomination of desolation that Daniel wrote about standing in the holy place then let those in Judea flee to the mountains, Luke said when you Jerusalem being surrounded by armies then you know its desolation is near and it will be time for those in Judea to flee to the mountains. Luke's Gentile audience would not have been familiar with Daniel's prophecies, so that's why Luke spelled it out to them instead of referencing something written by Daniel and saying "let the reader understand".
Honestly, I find the idea that Jesus spoke of two entirely different events where people in Judea had to flee to the mountains to be completely unreasonable.
The following is some of my reasoning, thus might not be what you are seeking, yet it's the best I can do for the time being.
In Daniel 12 I assume day 1335 is pertaining to the very last day of this age since it mentions no more days following that one, then considering what it says in the very last verse of that chapter.
Daniel 12:13 But go thou thy way till the end be: for thou shalt rest, and stand in thy lot at the end of the days.
Therefore, how can the preceding verse not be meaning this very end of the days in verse 13?
Daniel 12:10 Many shall be purified, and made white, and tried; but the wicked shall do wickedly: and none of the wicked shall understand; but the wise shall understand.
11 And from the time that the daily sacrifice shall be taken away, and the abomination that maketh desolate set up, there shall be a thousand two hundred and ninety days.
12 Blessed is he that waiteth, and cometh to the thousand three hundred and five and thirty days.
According to Daniel 11, when verse 10 above is meaning, it is meaning during the time Daniel 11:31 is meaning, which then is meaning when Jesus is meaning in Matthew 24:15.
What I am ultimately getting at here is this. If I am correct to connect Daniel 12:12 with that of Daniel 12:13 and the end of days, this alone proves that Daniel 12:11 and the time period involving 1290 days, that this 1290 days lead to the 1335th day in the end of this age. That means I am interpreting Matthew 24:15 correctly by placing those events in the end of this age rather than in the first century, because, clearly the end of days meant in Daniel 12:13 did not happen in the first century and is still unfulfilled as we speak.
In Daniel 12, verse 10 and 11 involve the time of trouble recorded in verse 1 in this same chapter. And in Matthew 24 Jesus places this same time of trouble in a context involving an AOD. And sure enough, in Daniel 12, verse 10 and 11 are also involving an AOD. To chalk these these things up us mere coincidences, thus no relation, is ludicrous, IMO. Nothing recorded in Daniel 12 could remotely be involving events pertaining to 70 AD, as in zero. Even verse 11 doesn't fit that time period since that would mean we have to apply verse 12 to that same time period. As if that makes some kind of good sense, that one was blessed in the first century by waiting and coming to the 1335th day.
Note: EDITED to add some things in order to try and make some points clearer, plus in order to try and fix some typos as well, of course..