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How do I advance with Mizuki? I am stuck at meet her at the office at daytime. Do I have to beat her at blackjack every time?

No. The event should trigger when you enter the office morning to afternoon.

Not too sure why it wouldn't trigger for u. That part has been working without issues and i never heard of players having problems there. Maybe try proceeding with other events.

I have basically gotten up to the point where I have the sewers with Asara as the only other active quest but Mizuki is still "go to the guard's office during daytime".

Might be a hint bug. Proceed with Asara. Also, what's the last Mizuki event u've done?

The Karaoke event. 

I did merge Mizu events with Willow's. Maybe sth broke for u. Did u update to 0.27 mid game?

What events did u do with Willow?

I did update, it might have broke something. I have done the Willow goes to the guard's office and that's where it stopped.

U should be able to fix it with the console. Check the m.story variable. Should be equal to 5. If it's not, then use m.story = 5

If that still doesn't help, try w.story = 2

Try entering both at home and then go to the office. Google renpy console if u don't know how to use it.