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I've been experimenting with this, see the attached structure, next to each item/project I have SHOWS/DOESN'T to indicate whether the Mac flagged item appears in the iPhone flagged view.

The surprises start down at 7 (a project structure I happen to use a lot). Tasks 7-2 and 7-3 are unavailable and shouldn't show up, but they do, whereas other unavailable tasks do not.

It looks like I was wrong, it's not that unavailability due to date that's a problem in the iPhone perspective, it's the unavailability due to structure is broken.

In short, there's no way to recreate the iPhone version of the flagged perspective on the iMac, it's doing something weird that doesn't fully map onto the Mac definition of "Availability".
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