...I don't understand the logic with the the 69th week lasting more than a thousand years...
I believe the 69th "week" will be a single year.
In the Hebrew, "week" is the word for "seven" (shebuah), which has for its root the word for "complete" (shaba), so that "week" may represent "completion," which may refer in a sealed manner to the completion of time we call a year.
I believe Daniel 9:24 could be saying that God would give physical Israel the 70 years it lost in their Babylonian captivity, but within those 70 years it must fulfill all righteousness.
This of course was not done and could not be done before Christ.
After Christ, the only commandment to restore the Jews to Jerusalem (Daniel 9:25) came in 1947 when the UN passed a resolution calling for the re-establishment of the state of Israel, something which had not existed since 70 AD.
Because of Daniel 9:25, I believe that from the commandment to restore the nation of physical Israel, there may be 7 years, and 62 years, and that in the 69th year Christ may come and fulfill all the requirements of Daniel 9:24 in "thy holy city" of physical Jerusalem, and in "thy holy people" of physical Israel (and so also fulfilling Isaiah 4:3-4), by the end of the 70th year, just as he fulfilled them in his spiritual kingdom at his 1st coming, but apart from physical Jerusalem (Hebrews 13:12, Luke 13:35) and apart from most of physical Israel (Matthew 21:43).