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I think you have to use dates ALL in the SAME year, too. So use 2017, or earlier. Not 2018..
Standing outside the courthouse, I just Alt-tabbed out of the game, turned back my system clock to let's say Jan 1 2017, with AC running in the background, then I went back into the game, entered the courthouse and talked to him. Then, I exited the building and waited for the spinning game-save icon to stop, then Alt-tabbed out of the game and repeated the process for each date... 12 times.
It was just a matter of making sure I was setting the right dates, while I was outside the courthouse, then entering the building and talking to Calendar Man with the date at the correct one.
That way, the game save triggered when I entered the building and the date was set correctly in the game, then talked to him, then exited the courthouse and generated another save, so that I got credit for that date.
Or...you can set aside an entire year, just remember to remind yourself of upcoming dates. :-)
PS: After I changed time 15x, my computer started to slows down and after a day it was completely freezes, I thought I have some viruses, but at the end I think there were so much updates because of changed time that computer freezed.